3314-30-5|1H-Benzo[d]imidazole-2-carbaldehyde| Ambeed

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Quality Control of [ 3314-30-5 ] Purity: 95% SDS Specification

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Product Details of [ 3314-30-5 ]

CAS No. :	3314-30-5
Formula :	C₈H₆N₂O
M.W :	146.15
SMILES Code :	O=CC1=NC2=CC=CC=C2N1
MDL No. :	MFCD00228045
InChI Key :	DQOSJWYZDQIMGM-UHFFFAOYSA-N
Pubchem ID :	76826

Safety of [ 3314-30-5 ]

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

Computational Chemistry of [ 3314-30-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	41.48
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.75 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.35
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	1.05
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.38
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.	0.35
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	2.17
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.06

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.95
Solubility	1.65 mg/ml ; 0.0113 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.	-1.6
Solubility	3.66 mg/ml ; 0.025 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	-2.84
Solubility	0.213 mg/ml ; 0.00146 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.	-6.45 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)	1.13

Application In Synthesis of [ 3314-30-5 ]

* 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 [ 3314-30-5 ]

[ 3314-30-5 ] Synthesis Path-Downstream 1~35

1
[ 615-15-6 ]
[ 3314-30-5 ]

References: [1]Journal of the Indian Chemical Society,1982,vol. 59,p. 349 - 351.
[2],1959,vol. 8,p. 1037.
[3]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594.

2
[ 3314-30-5 ]
[ 151-50-8 ]
[ 101278-94-8 ]

References: [1]Patent: DE947610,1956, .

3
[ 3314-30-5 ]
[ 2849-93-6 ]

References: [1]Journal of Biological Chemistry,1958,vol. 230,p. 511,513 Anm. 3.

4
[ 4856-97-7 ]
[ 3314-30-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With manganese(IV) oxide; In dichloromethane; at 40℃; for 2h;	To a solution of 1 (5.0 g, 34 mmol) in DCM was added MnO2(1.3 g, 6.8 mmol). The resulting solution was stirred at 40 C for 2 h and monitored by TLC. Aftercomplete conversion of starting material, reaction mixture was cooled to room temperature, filteredand concentrated in vacuo to obtain 2 as white solid in 85.0% yield. LC-MS m/z: 147.1 [M + H]+.
70%	With [Ru(2,6-bis[1-(pyridin-2-yl)-1H-benzo[d]-imidazol-2-yl]pyridine)(pyridine-2,6-dicarboxylate)]; dihydrogen peroxide; In water; at 50℃; for 5.5h;Catalytic behavior;	The procedure for gram scale oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehydewas as follows: (1H-benzo[d]imidazol-2-yl)methanol (0.1 mol,14.8 g) and [Ru(bpbp)(pydic)] (0.001 mmol, 7.32 × 10-3 g) wereadded into a reactor. The reactor containing this mixture was heatedto 50 C in an oil bath under vigorous stirring and then 30% H2O2(30 mL, 0.3 mol) was slowly dropwise over a period of 30 min. The mixture was stirred for 5 h. After filtering, the solution wasevaporation under reduced pressure at 50 C. Pure 1H-benzo[d]imidazole-2-carbaldehyde (0.07 mmol, 10.2 g) was obtained with ayield of 70% after recrystallisation from 30% H2SO4 solution. Theproduct, 1H-benzo[d]imidazole-2-carbaldehyde, was identified byits 1H NMR spectrum.
57%	With Ru(bpp)(pydic); dihydrogen peroxide; at 50℃;	The method for synthesizing 2-aldehyde benzimidazole in this example is as follows2-Hydroxymethylbenzimidazole (0.1 mol, 14.8 g)The rhodium complex (10-4 mol, 0.0577 g) in Example 1 was added to the reaction vessel.Hydrogen peroxide (30%, 0.3 mol, 9.1 ml) was slowly added to the reaction vessel with stirring.The reaction temperature was controlled at 50C for several hours.The reaction solution was concentrated under reduced pressure,Obtain a solid product,The solid product was dissolved in dichloromethane and subjected to silica gel column chromatography.Get pure product2-aldehyde benzoimidazole 8.32 g,Yield 57%.

51%	With manganese(IV) oxide; In methanol; dichloromethane;	General procedure: To a stirred solution of the (1H-benzo[d]imidazol-2-yl)methanol from above (2.6 mmol) in dryCH2Cl2/MeOH (6:1, 3.5 mL) was added activated manganese dioxide (85% purity, <5 micron, 2.328 g, 22.8 mmol)and the suspension stirred overnight, at which point the black slurry was filtered through a cake of celite andwashed with MeOH (3x5 mL). The combined washings were concentrated to afford a dark brown solid.Purification of the crude product by column chromatography on silica gel (CH2Cl2:MeOH, 98:2 to 95:5) affordedthe title compound 1H-benzo[d]imidazole-2-carbaldehyde (2i) (0.245 g, 51%).
	With manganese(IV) oxide; In ethyl acetate; at 65℃; for 1h;	General procedure: A solution of 2a-2d (2 mmol), MnO2 (3.48 g, 40 mmol) was added to EtOAc (120 mL), then refluxedat 65 C for 1 h (monitored by TLC). Afterwards the solution was filtered, and concentrated in vacuoto give pure compounds 3a-3d (in 60%-76% yield) [17].
	With manganese(IV) oxide; In dichloromethane; at 40℃; for 2h;	The resulting solid (1H-benzimidazol-2-yl) methanol (34 mmol) was dissolved in 250 mL of dichloromethane and stirredFollowed by addition of manganese dioxide (0.68 mmol). The temperature was raised to 40 C and stirring was continued for 2 hours to monitor the reaction. After the reaction is complete, the product is evaporated to drynessDichloromethane, 150 mL of tetrahydrofuran was added. Directly to the next step
	With manganese dioxide; In N-methyl-acetamide; ethanol;	EXAMPLE I STR28 A mixture of 2-Hydroxymethyl-benzimidazole (11.9 g) and MnO2 (59.5 g) in ethanol (250 mL) was vigorously stirred for 2 days. The reaction was concentrated in vacuo, hot dimethylformamide was added and the mixture was filtered through celite. After removal of the solvent in vacuo the tan solid was triturated with ethanol to afford 2-Benzimidazolecarboxaldehyde as a tan powder.

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 3128 - 3130.
[2]Journal of Fluorescence,2011,vol. 21,p. 2005 - 2013.
[3]Molecules,2019,vol. 24.
[4]Journal of the Chemical Society. Perkin transactions I,1982,p. 2871 - 2876.
[5]Angewandte Chemie - International Edition,1998,vol. 37,p. 1270 - 1273.
[6]Journal of Chemical Research,2017,vol. 41,p. 88 - 92.
[7]Canadian Journal of Chemistry,2003,vol. 81,p. 612 - 619.
[8]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 1765 - 1767.
[9]Patent: CN107445998,2017,A .Location in patent: Paragraph 0028-0031.
[10]Synthesis,2015,vol. 47,p. 1913 - 1921.
[11]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594.
[12]Molecules,2016,vol. 21.
[13]Patent: CN107118249,2017,A .Location in patent: Paragraph 0120; 0121; 0122.
[14]Patent: US5610299,1997,A .

5
[ 5466-57-9 ]
[ 144-62-7 ]
[ 3314-30-5 ]

References: [1]Angewandte Chemie,1956,vol. 68,p. 151.

6
[ 13109-82-5 ]
[ 3314-30-5 ]

References: [1]Patent: DE942327,1953, .
[2]Chemische Berichte,1956,vol. 89,p. 689,691.

7
[ 584-12-3 ]
[ 3314-30-5 ]
[ 24898-47-3 ]

References: [1]Journal of Organic Chemistry,1962,vol. 27,p. 3236 - 3239.

8
[ 1003-09-4 ]
[ 3314-30-5 ]
[ 24898-45-1 ]

References: [1]Journal of Organic Chemistry,1962,vol. 27,p. 3236 - 3239.

9
[ 3314-30-5 ]
1,3-dimethyl-6,7-dimethoxy-2-benzopyrylium perchlorate [ No CAS ]
1-[2-(1<i>H</i>-benzoimidazol-2-yl)-vinyl]-6,7-dimethoxy-3-methyl-isochromenylium; perchlorate [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1973,vol. 9,p. 527 - 528.
Khimiya Geterotsiklicheskikh Soedinenii,1973,vol. 9,p. 568 - 569.

10
[ 3314-30-5 ]
[ 79-40-3 ]
[ 27396-06-1 ]

References: [1]Journal of Heterocyclic Chemistry,1970,vol. 7,p. 457 - 462.

11
[ 3314-30-5 ]
[ 137-07-5 ]
[ 30418-55-4 ]

References: [1]Journal of medicinal chemistry,1971,vol. 14,p. 248 - 251.

12
[ 288-32-4 ]
[ 3314-30-5 ]
[ 122-52-1 ]
[ 78645-33-7 ]
[ 78645-31-5 ]

References: [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 636 - 638.
Zhurnal Obshchei Khimii,1981,vol. 51,p. 775 - 778.

13
[ 51-17-2 ]
[ 3314-30-5 ]
[ 762-04-9 ]
[ 78645-32-6 ]

References: [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 636 - 638.
Zhurnal Obshchei Khimii,1981,vol. 51,p. 775 - 778.

14
[ 51-17-2 ]
[ 3314-30-5 ]
[ 122-52-1 ]
[ 78645-34-8 ]
[ 78645-32-6 ]

References: [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 636 - 638.
Zhurnal Obshchei Khimii,1981,vol. 51,p. 775 - 778.

15
[ 67-56-1 ]
[ 3314-30-5 ]
[ 13616-10-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 158 - 159.

16
[ 3314-30-5 ]
[ 33803-58-6 ]
[ 118448-69-4 ]

References: [1]Pharmaceutical Chemistry Journal,1988,vol. 22,p. 750 - 754.
Khimiko-Farmatsevticheskii Zhurnal,1988,vol. 22,p. 1188 - 1193.

17
[ 3314-30-5 ]
[ 118-92-3 ]
2-<(1H-benzimidazol-2-ylmethylene)amino>benzoic acid [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1984,vol. 61,p. 757 - 759.

18
[ 3314-30-5 ]
[ 62-53-3 ]
[ 762-04-9 ]
[ 78645-30-4 ]
[ 78645-29-1 ]

References: [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 636 - 638.
Zhurnal Obshchei Khimii,1981,vol. 51,p. 775 - 778.
[2]Russian Journal of General Chemistry,1998,vol. 68,p. 1467 - 1476.

19
[ 3314-30-5 ]
[ 119-26-6 ]
[ 77200-84-1 ]

References: [1]Pharmazie,1980,vol. 35,p. 585 - 586.

20
[ 3314-30-5 ]
[ 95-85-2 ]
2-<(1H-benzimidazole-2-ylmethylene)amino>-4-chlorophenol [ No CAS ]

References: [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1984,vol. 23,p. 79 - 80.

21
[ 3314-30-5 ]
[ 99-57-0 ]
2-<(1H-benzimidazole-2-ylmethylene)amino>-4-nitrophenol [ No CAS ]

References: [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1984,vol. 23,p. 79 - 80.

22
[ 3314-30-5 ]
[ 4114-31-2 ]
benzimidazole-2-carbaldehyde ethoxycarbonylhydrazone [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1984,p. 3701 - 3711.

23
[ 5466-57-9 ]
[ 3314-30-5 ]

Yield	Reaction Conditions	Operation in experiment
85.3%	With sulfuric acid; In water; at 80℃; for 1h;	15 mL (276 mmol, 6.6 eq) of concentrated sulfuric acid was slowly added dropwise to 8.40 g (41.8 mmol) of compound L5, Yellow bubbles, 10min after the drop is completed, At this time compound L5 is completely dissolved, The oil bath was heated at 80 ° C for 1 h and the reaction was stopped. Cold to room temperature, Add 150mL ice water, 4N NaOH aqueous solution adjusted to pH 7, At this time the original transparent solution in the precipitation of yellow solid, Filter, drying, Get 5.21g, The yield was 85.3percent. To give 1H-benzimidazole-2-formaldehyde,Compound code L6.

References: [1]Patent: CN104211632,2016,B .Location in patent: Paragraph 0131; 0132.
[2]Pharmazie,1980,vol. 35,p. 585 - 586.

24
[ 3314-30-5 ]
[ 3132-64-7 ]
[ 76098-96-9 ]

References: [1]European Journal of Medicinal Chemistry,1980,vol. 15,p. 199 - 205.

25
[ 110-00-9 ]
[ 3314-30-5 ]
[ 24898-47-3 ]