38956-79-5|3-Hydrazinyl-6-methylpyridazine| Ambeed

Structure of 38956-79-5

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Quality Control of [ 38956-79-5 ] Purity: 98% SDS Specification

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Product Details of [ 38956-79-5 ]

CAS No. :	38956-79-5
Formula :	C₅H₈N₄
M.W :	124.14
SMILES Code :	N(N)C1=CC=C(N=N1)C
MDL No. :	MFCD00067771
InChI Key :	FIEDFVRFAQARPW-UHFFFAOYSA-N
Pubchem ID :	12379804

Safety of [ 38956-79-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 38956-79-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	34.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.83 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.86
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.18
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.12
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.05
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.11
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.1

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.92
Solubility	14.8 mg/ml ; 0.119 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.7
Solubility	24.5 mg/ml ; 0.197 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.69
Solubility	2.55 mg/ml ; 0.0205 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.19 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.96

Application In Synthesis of [ 38956-79-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 38956-79-5 ]

[ 38956-79-5 ] Synthesis Path-Downstream 1~35

1
[ 65202-58-6 ]
[ 38956-79-5 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 1259 - 1261.

2
[ 38956-79-5 ]
[ 1694-31-1 ]
[ 69579-14-2 ]

References: [1]European Journal of Medicinal Chemistry,1984,vol. 19,p. 111 - 117.

3
[ 38956-79-5 ]
[ 123-76-2 ]
[ 77505-41-0 ]

References: [1]European Journal of Medicinal Chemistry,1984,vol. 19,p. 111 - 117.

4
[ 38956-79-5 ]
[ 762-42-5 ]
[ 110363-99-0 ]

References: [1]Acta Chimica Hungarica,1986,vol. 122,p. 211 - 215.

5
[ 38956-79-5 ]
[ 110364-01-7 ]

References: [1]Acta Chimica Hungarica,1986,vol. 122,p. 211 - 215.

6
[ 38956-79-5 ]
[ 110364-05-1 ]

References: [1]Acta Chimica Hungarica,1986,vol. 122,p. 211 - 215.

7
[ 38956-79-5 ]
[ 741288-28-8 ]
[ 858600-53-0 ]

Yield	Reaction Conditions	Operation in experiment
23%		4) 1-(6-Methyl-3-pyridazinyl)-5-(5-methyl-2-pyridyl)-1H-pyrazole-3-carboxylic acid ethyl ester To a solution of 4-(5-methyl-2-pyridyl)-2, 4-dioxobutanoic acid ethyl ester (3.54 g) and <strong>[38956-79-5]3-hydrazino-6-methylpyridazine</strong> (1.87 g) of (1) above in ethanol (71 mL), acetic acid (4.31 mL) was added at room temperature, and the resultant mixture was heated to reflux for 15 hours. Further, concentrated hydrochloric acid (4.7 mL) was added to the reaction solution, and the mixture was heated to reflux for 3 hours. After air cooling, saturated sodium hydrogen carbonate and chloroform were added to the reaction solution, and the mixture was partitioned. The organic layer was dried over anhydrous sodium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (chloroform-ethyl acetate), to obtain 1-(6-methyl-3-pyridazinyl)-5-(5-methyl-2-pyridyl)-1H-pyrazole-3-carboxylic acid ethyl ester (1.13 g, 23%) as a solid. 1H-NMR(400MHz, CDCl3)delta: 1.41-1.44(3H, m), 2.32(3H, s), 2.72(3H, s), 4.43-4.48(2H, m), 7.18(1H, s), 7.46-7.56(3H, m), 7.98(1H, d, J=8.8Hz), 8.21(1H, m). EI-MSm/z: 323(M+).

References: [1]Patent: EP1785418,2007,A1 .Location in patent: Page/Page column 38-39.

8
[ 72093-07-3 ]
[ 38956-79-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrazine; In ethanol; for 2.5h;Heating / reflux;Product distribution / selectivity;	1) 3-Hydrazino-6-methylpyridazine Hydrazine monohydrate (45 mL) was added to a suspension of 3-chloro-6-methylpyridine (3.00 g) in ethanol (45 mL), and the resultant mixture was heated to reflux for 2.5 hours. After air cooling, a residue obtained by evaporating the reaction solvent was purified by silica gel chromatography (a lower layer mixed solvent of chloroform-methanol-water (7:3:1)), to obtain 3-hydrazino-6-methylpyridazine (2.35 g, 81%) as a solid. 1H-NMR(400MHz, DMSO-d6)delta: 2.39(3H, s), 4.20(2H, br), 6.94(1H, d, J=9.3Hz), 7.18(1H, d, J=9.3Hz), 7.64(1H, br). ESI-MSm/z: 125(M+H)+.

References: [1]Patent: EP1785418,2007,A1 .Location in patent: Page/Page column 38.

9
[ 75-15-0 ]
[ 38956-79-5 ]
[ 89418-40-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium hydroxide; In methanol; at 0 - 20℃;Heating / reflux;	Step 2: 6-Methyl-[l,2,4]triazoIo[4,3-b]pyridazine-3-thiol; [0373] To a solution of KOH (1 1.3 g, 0.202 mol) in methanol (100 mL) was added (6- methyl-pyridazin-3-yl)-hydrazine (25 g, 0.202 mol) at room temperature. The reaction mixture was placed in an ice-water bath and carbon disulfide (98 mL, 1.61 mol) was slowly added. The resultant yellow solution was heated to reflux overnight before removal of solvent. The yellow residue was acidified with 2 N aqueous HCl to pH~4, filtered, and washed with water. Upon drying 33 g of 6-methyl-[l, 2,4]triazolo [4,3 -b]pyridazine-3 -thiol was obtained as a yellow powder (85% yield): 1HNMR (DUSO-d6): delta 2.5 (s, 3H), 7.28 (d, IH), 8.05 (d, IH), 14.66 (br s, IH); MS (m/z) 167 [M+H+]+.

References: [1]Patent: WO2008/51808,2008,A2 .Location in patent: Page/Page column 107.

10
[ 38956-79-5 ]
3-cyclopropyl-6-methyl[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

11
[ 38956-79-5 ]
[ 3132-99-8 ]
3-(3-bromophenyl)-6-methyl[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

12
[ 38956-79-5 ]
[ 3132-99-8 ]
C₁₂H₁₁BrN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

13
[ 38956-79-5 ]
[ 64622-16-8 ]
3-(2-bromo-6-chlorophenyl)-6-methyl[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

14
[ 38956-79-5 ]
[ 64622-16-8 ]
C₁₂H₁₀BrClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

15
[ 38956-79-5 ]
[ 83-38-5 ]
3-(2,6-dichlorophenyl)-6-methyl[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

16
[ 38956-79-5 ]
[ 83-38-5 ]
C₁₂H₁₀Cl₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

17
[ 38956-79-5 ]
[ 57848-46-1 ]
3-(4-bromo-2-fluorophenyl)-6-methyl[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

18
[ 38956-79-5 ]
[ 57848-46-1 ]
C₁₂H₁₀BrFN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

19
[ 38956-79-5 ]
[ 93118-03-7 ]
C₁₃H₁₀ClF₃N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

20
[ 38956-79-5 ]
[ 1571-08-0 ]
C₁₄H₁₄N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

21
[ 38956-79-5 ]
[ 1571-08-0 ]
methyl 4-(6-methyl[1,2,4]triazolo[4,3-b]pyridazin-3-yl)benzoate [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

22
[ 38956-79-5 ]
[ 619-66-9 ]
C₁₃H₁₂N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

23
[ 38956-79-5 ]
[ 619-66-9 ]
4-(6-methyl[1,2,4]triazolo[4,3-b]pyridazin-3-yl)benzoic acid [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

24
[ 38956-79-5 ]
[ 105-07-7 ]
C₁₃H₁₁N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.

25
[ 38956-79-5 ]
[ 105-07-7 ]
4-(6-methyl[1,2,4]triazolo[4,3-b]pyridazin-3-yl)benzonitrile [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.

26
[ 38956-79-5 ]
[ 99-61-6 ]
C₁₂H₁₁N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

27
[ 38956-79-5 ]
[ 99-61-6 ]
6-methyl-3-(3-nitrophenyl)[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.

28
[ 38956-79-5 ]
[ 63697-96-1 ]
3-(4-ethynylphenyl)-6-methyl[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

29
[ 38956-79-5 ]
[ 63697-96-1 ]
C₁₄H₁₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

30
[ 14371-10-9 ]
[ 38956-79-5 ]
6-methyl-3-[(E)-2-phenylethenyl][1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.

31
[ 14371-10-9 ]
[ 38956-79-5 ]
C₁₄H₁₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.

32
[ 498-62-4 ]
[ 38956-79-5 ]
6-methyl-3-(thiophen-3-yl)[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

33
[ 498-62-4 ]
[ 38956-79-5 ]
C₁₀H₁₀N₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

34
[ 872-85-5 ]
[ 38956-79-5 ]
6-methyl-3-(pyridin-4-yl)[1,2,4]triazolo[4,3-b]pyridazine [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

35
[ 872-85-5 ]
[ 38956-79-5 ]
C₁₁H₁₁N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 38956-79-5 ]

Amines

A422334 [61070-99-3]

Pyridazine-3,6-diamine

Similarity: 0.62

A261847 [5469-69-2]

3-Amino-6-chloropyridazine

Similarity: 0.51

Related Parent Nucleus of
[ 38956-79-5 ]

Pyridazines

A168540 [1632-76-4]

3-Methylpyridazine

Similarity: 0.68

A422334 [61070-99-3]

Pyridazine-3,6-diamine

Similarity: 0.62

A150558 [37444-46-5]

Pyridazin-3-ylmethanol

Similarity: 0.58

A334396 [1121-79-5]

3-Chloro-6-methylpyridazine

Similarity: 0.55

A113537 [65202-58-6]

3-Bromo-6-methylpyridazine

Similarity: 0.52

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
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P222	Do not allow contact with air.
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Response
Code	Phrase
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P321
P322
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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Storage
Code	Phrase
P401
P402	Store in a dry place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
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P422
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
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H332	Harmful if inhaled
H333	May be harmful if inhaled
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 38956-79-5

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