939-83-3|2-Methyl-5-nitrobenzonitrile| Ambeed

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Quality Control of [ 939-83-3 ] Purity: 97% SDS Specification

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Product Details of [ 939-83-3 ]

CAS No. :	939-83-3
Formula :	C₈H₆N₂O₂
M.W :	162.15
SMILES Code :	C1=C(C=CC(=C1C#N)C)[N+](=O)[O-]
MDL No. :	MFCD00017040
InChI Key :	XOSDYLFXPMFRGF-UHFFFAOYSA-N
Pubchem ID :	350143

Safety of [ 939-83-3 ]

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

Computational Chemistry of [ 939-83-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	44.94
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	69.61 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.37
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	2.27
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.77
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.	0.59
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	0.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.58
Solubility	0.427 mg/ml ; 0.00263 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.37
Solubility	0.0694 mg/ml ; 0.000428 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-2.24
Solubility	0.931 mg/ml ; 0.00574 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	Yes
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	Yes
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.	-5.68 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	2.0 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)	1.94

Application In Synthesis of [ 939-83-3 ]

* 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 [ 939-83-3 ]

[ 939-83-3 ] Synthesis Path-Downstream 1~35

1
[ 110-89-4 ]
[ 939-83-3 ]
[ 100-52-7 ]
[ 61599-49-3 ]

References: [1]Bulletin de la Societe Chimique de France,1939,vol. <5> 6,p. 1182,1187.
[2]Chemische Berichte,1908,vol. 41,p. 2296.

2
[ 120-57-0 ]
[ 939-83-3 ]
2-(trans(?)-2-benzo[1,3]dioxol-5-yl-vinyl)-5-nitro-benzoic acid amide [ No CAS ]

References: [1]Chemische Berichte,1944,vol. 77/79,p. 487,494.
Bl. scient. Acad. roum.,1946,vol. 28,p. 413,423.

3
[ 120-57-0 ]
[ 939-83-3 ]
2-(trans(?)2-benzo[1,3]dioxol-5-yl-vinyl)-5-nitro-benzonitrile [ No CAS ]

References: [1]Chemische Berichte,1944,vol. 77/79,p. 487,494.
Bl. scient. Acad. roum.,1946,vol. 28,p. 413,423.

4
[ 529-19-1 ]
[ 939-83-3 ]

References: [1]Organic Letters,2003,vol. 5,p. 1131 - 1134.
[2]Journal of Materials Chemistry,2011,vol. 21,p. 9523 - 9531.
[3]Chemische Berichte,1898,vol. 31,p. 2884.
[4]Chemische Berichte,1898,vol. 31,p. 2884.
[5]Chemische Berichte,1918,vol. 51,p. 561.
[6]Helvetica Chimica Acta,1922,vol. 5,p. 58.
[7]Journal of the American Chemical Society,1961,vol. 83,p. 4564 - 4571.
[8]Journal of the Chemical Society. Perkin transactions I,1973,p. 2940 - 2948.

5
[ 939-83-3 ]
[ 528-46-1 ]
2'-cyano-4'-nitro-stilbene-2-carboxylic acid [ No CAS ]

References: [1]Chemische Berichte,1911,vol. 44,p. 1122.

6
[ 939-83-3 ]
[ 1975-52-6 ]

References: [1]Journal of the Indian Chemical Society,1937,vol. 14,p. 144,150.
[2]Patent: WO2006/117669,2006,A1 .

7
[ 939-83-3 ]
[ 50825-99-5 ]

References: [1]Chemische Berichte,1941,vol. 74,p. 1279,1284.
[2]Chemische Berichte,1898,vol. 31,p. 2884.

8
[ 939-83-3 ]
[ 28169-46-2 ]

References: [1]Bulletin de la Societe Chimique de France,1938,vol. <5> 5,p. 1350,1356.

9
[ 939-83-3 ]
6,6'-dimethyl-3,3'-hydrazo-di-benzonitrile [ No CAS ]
[ 50670-64-9 ]

References: [1]Bulletin de la Societe Chimique de France,1938,vol. <5> 5,p. 1350,1356.

10
[ 939-83-3 ]
[ 50670-64-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen;palladium 10% on activated carbon; In ethanol; ethyl acetate;	Step 2: 5-Amino-2-methylbenzonitrile: A mixture of <strong>[939-83-3]2-methyl-5-nitrobenzonitrile</strong> (25.0 g, 154 mmol), 10% palladium on charcoal (2.5 g) ethyl acetate (150 mL) and ethanol (150 mL) is stirred under an atmosphere of hydrogen. The catalyst is removed by filtration through a pad of celite and the filtrate is concentrated to give 5-amino-2-methylbenzonitrile (also see, Scholz, D. et al. J. Med Chem., 41,1050-1059 (1998)) (19.6 g, 96%) as a tan solid. MS: m/e = 133 (M + H).
59.6%	palladium; In ethanol; ethyl acetate;	EXAMPLE XV 3-Amino-6-methylbenzonitrile STR25 A suspension of 8.11 g (50 mmol) of 6-methyl-3-nitrobenzonitrile and 0.81 g of 10% of palladium-on-charcoal in 50 ml of ethanol and 50 ml of ethyl acetate is hydrogenated under 2.9 bar for 1 hour. The catalyst is filtered off, the filtrate is concentrated and the residue is crystallized from ether/petroleum ether. Yield: 59.6% of theory Melting point: 88 C.
	With iron; ammonium chloride; In 1,4-dioxane; ethanol; water; at 25 - 80℃; for 16.0h;	Step 1. Preparation of 5-amino-2-methyl-benzonitrile (B18-1): A stirred suspension of <strong>[939-83-3]2-methyl-5-nitro benzonitrile</strong> (20 g, 123.45 mmol) in a mixture of dioxane (640 mL), ethanol (480 mL) and water (160 mL) at 25 C. was treated with NH4Cl (26.4 g, 493.8 mmol) followed by treatment with iron powder (34.4 g, 617.2 mmol). The mixture was then heated at 80 C. for 16 hours. The mixture was filtered through a Celite bed and concentrated. The resultant residue was diluted with EtOAc (600 mL), washed with water (150 mL) and brine (100 mL), and dried over anhydrous sodium sulfate. The organic solution was then concentrated to provide B18-1 as an orange solid. Yield: 18.2 g. 1H NMR (CDCl3): delta 7.08 (d, 1H), 6.84-6.9 (m, 1H), 6.75-6.82 (m, 1H), 3.65-3.82 (m, 2H) and 2.4 (s, 3H). Mass: (M+1) 133 calculated for C8H8N2. The product was used below to prepare B18-2 without further purification.

References: [1]Patent: WO2005/97750,2005,A1 .Location in patent: Page/Page column 69.
[2]Organic Letters,2017,vol. 19,p. 4746 - 4749.
[3]Organic Letters,2003,vol. 5,p. 1131 - 1134.
[4]Journal of Materials Chemistry,2011,vol. 21,p. 9523 - 9531.
[5]Patent: US5596006,1997,A .
[6],1949,vol. <A> 1,p. 253,257.
Chem.Abstr.,1952,p. 937.
[7]Chemische Berichte,1898,vol. 31,p. 2884.
[8]Justus Liebigs Annalen der Chemie,1941,vol. 546,p. 277,291.
[9]Patent: US2009/54395,2009,A1 .Location in patent: Page/Page column 45.

11
[ 939-83-3 ]
4,4'-dinitro-stilbene-2,2'-dicarbonitrile [ No CAS ]

References: [1]Journal of the Chemical Society,1907,vol. 91,p. 2080.

12
[ 939-83-3 ]
[ 712-97-0 ]
5-nitro-2-[trans(?)-2-(6-nitro-benzo[1,3]dioxol-5-yl)-vinyl]-benzoic acid amide [ No CAS ]

References: [1]Chemische Berichte,1944,vol. 77/79,p. 487,494.
Bl. scient. Acad. roum.,1946,vol. 28,p. 413,423.

13
[ 939-83-3 ]
[ 99-61-6 ]
4,3'-dinitro-trans-stilbene-carboxylic acid-⁽²⁾-amide [ No CAS ]

References: [1]Chemische Berichte,1944,vol. 77/79,p. 487,494.
Bl. scient. Acad. roum.,1946,vol. 28,p. 413,423.

14
[ 939-83-3 ]
[ 555-16-8 ]
4,4'-dinitro-trans-stilbene-carboxylic acid-⁽²⁾-amide [ No CAS ]

References: [1]Chemische Berichte,1944,vol. 77/79,p. 487,494.
Bl. scient. Acad. roum.,1946,vol. 28,p. 413,423.

15
[ 939-83-3 ]
[ 124-41-4 ]
[ 100-52-7 ]
[ 61599-50-6 ]

References: [1]Chemische Berichte,1941,vol. 74,p. 1279,1284.

16
[ 939-83-3 ]
[ 100-52-7 ]
[ 61599-49-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 485 - 488.
[2]Journal of Chemical Research,2005,p. 138 - 140.
[3]Chemische Berichte,1908,vol. 41,p. 2296.

17
[ 939-83-3 ]
[ 123-08-0 ]
[ 61599-51-7 ]

References: [1]Chemische Berichte,1916,vol. 49,p. 2440.
Chemische Berichte,1918,vol. 51,p. 562.

18
[ 939-83-3 ]
[ 123-11-5 ]
[ 61599-52-8 ]

19
[ 939-83-3 ]
[ 591-31-1 ]
4-nitro-3'-methoxy-trans-stilbene-carbonitrile-⁽²⁾ [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1938,vol. <5> 5,p. 1350,1356.

20
[ 939-83-3 ]
[ 135-02-4 ]
2'-methoxy-4-nitro-stilbene-2-carbonitrile [ No CAS ]

References: [1]Chemische Berichte,1916,vol. 49,p. 2440.
Chemische Berichte,1918,vol. 51,p. 562.

21
[ 939-83-3 ]
[ 100-10-7 ]
[ 61599-53-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 485 - 488.
[2]Chemische Berichte,1915,vol. 48,p. 1796.
Chemische Berichte,1916,vol. 49,p. 2433,2440.
[3]Journal of Materials Chemistry,1997,vol. 7,p. 625 - 630.

22
[ 939-83-3 ]
[ 613-45-6 ]
[ 106987-30-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 485 - 488.
[2]Journal fur praktische Chemie (Leipzig 1954),1925,vol. <2> 109,p. 221.
Justus Liebigs Annalen der Chemie,1925,vol. 441,p. 248.

23
[ 939-83-3 ]
[ 122-03-2 ]
4'-isopropyl-4-nitro-stilbene-2-carbonitrile [ No CAS ]

References: [1]Chemische Berichte,1918,vol. 51,p. 561.

24
[ 939-83-3 ]
[ 552-89-6 ]
4,2'-dinitro-trans-stilbene-carboxylic acid-⁽²⁾-amide [ No CAS ]

References: [1]Chemische Berichte,1941,vol. 74,p. 1279,1284.

25
[ 626-19-7 ]
[ 939-83-3 ]
[ 2695-76-3 ]

References: [1]Bulletin de la Societe Chimique de France,1965,p. 1858 - 1862.

26
[ 626-19-7 ]
[ 939-83-3 ]
[ 2695-75-2 ]

References: [1]Bulletin de la Societe Chimique de France,1965,p. 1858 - 1862.

27
[ 939-83-3 ]
[ 623-27-8 ]
[ 2695-71-8 ]

References: [1]Bulletin de la Societe Chimique de France,1965,p. 1858 - 1862.

28
[ 939-83-3 ]
[ 623-27-8 ]
[ 2695-70-7 ]

References: [1]Bulletin de la Societe Chimique de France,1965,p. 1858 - 1862.

29
[ 110-86-1 ]
[ 117-80-6 ]
[ 939-83-3 ]
[ 109386-32-5 ]