[ CAS No. 10394-40-8 ] {[proInfo.proName]}

Name: 10394-40-8|1,6-Dimethyl-1H-benzo[d]imidazole|97%
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SKU: A119595
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Quality Control of [ 10394-40-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 10394-40-8 ]

SDS Specification

Alternatived Products of [ 10394-40-8 ]

Product Details of [ 10394-40-8 ]

CAS No. :	10394-40-8	MDL No. :	MFCD08685462
Formula :	C₉H₁₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FARVSSLSGAIQMM-UHFFFAOYSA-N
M.W :	146.19	Pubchem ID :	14856790
Synonyms :

Calculated chemistry of [ 10394-40-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.96
TPSA :	17.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	1.8
Log Po/w (WLOGP) :	1.88
Log Po/w (MLOGP) :	1.63
Log Po/w (SILICOS-IT) :	1.91
Consensus Log Po/w :	1.8

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.478 mg/ml ; 0.00327 mol/l
Class :	Soluble
Log S (Ali) :	-1.79
Solubility :	2.35 mg/ml ; 0.0161 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.84
Solubility :	0.212 mg/ml ; 0.00145 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.23

Safety of [ 10394-40-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 10394-40-8 ]

* 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.

Upstream synthesis route of [ 10394-40-8 ]
Downstream synthetic route of [ 10394-40-8 ]

[ 10394-40-8 ] Synthesis Path-Upstream 1~12

1
[ 65081-42-7 ]
[ 149-73-5 ]
[ 10394-40-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid In methanol at 20℃; for 5 h;	Step B: Preparation of 1 ,6-dimethyl- 1H-benzo [dlimidazole: N,5 -dimethyl-2- nitro-aniline (20.2 g, 122 mmol), trimethyl orthoformate (133 mL, 1216 mmol), 10percent palladium on carbon (6.47 g, 6.1 mmol) and p-toluenesulfonic acid monohydrate (2.31 g, 12.2 mmol) in methanol (240 mL) was placed under 1 atmosphere of hydrogen with balloon and stirred at ambient temperature for 5 hours. Catalyst was removed by filtration and washed with methanol (200 mL). The filtrate was concentrated under reduced pressure. The residue was treated withsaturated sodium bicarbonate (50 mL) and ethyl acetate (300 mL). The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give 1,6-dimethylbenzimidazole (17.7 g, quantitative) as solid.

Reference： [1] Patent: WO2015/175845, 2015, A1, . Location in patent: Paragraph 0307; 0394

2
[ 131019-87-9 ]
[ 10394-40-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With formic acid In hydrogenchloride; water	STR43 A mixture of 6.60 g of 1-amino-4-methyl-2-(N-methylamino)benzene and a solution of 3.5 ml of formic acid in 50 ml of a 4N HCl was stirred at 100° C. for 3.5 hours. The reaction solution was concentrated under reduced pressure and water was added to the residue. After washing with ethyl acetate, the aqueous phase was rendered alkaline with aqueous potassium carbonate followed by extraction with chloroform. The chloroform layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (40 g). Elution with ethyl acetate followed by recyrstallization from ethyl acetate-hexane gave 4.01 g (57percent) of 1,6-dimethylbenzimidazole.

Reference： [1] Patent: US4977175, 1990, A,

3
[ 67-56-1 ]
[ 89-62-3 ]
[ 10394-40-8 ]
[ 10394-35-1 ]
[ 614-97-1 ]

Reference： [1] Green Chemistry, 2015, vol. 17, # 12, p. 5172 - 5181

4
[ 67-56-1 ]
[ 496-72-0 ]
[ 10394-40-8 ]
[ 10394-35-1 ]
[ 614-97-1 ]

Reference： [1] Green Chemistry, 2015, vol. 17, # 12, p. 5172 - 5181

5
[ 614-97-1 ]
[ 74-88-4 ]
[ 10394-40-8 ]

Reference： [1] ChemCatChem, 2018, vol. 10, # 19, p. 4338 - 4345

6
[ 446-34-4 ]
[ 10394-40-8 ]

Reference： [1] Patent: WO2015/175845, 2015, A1,

7
[ 65081-42-7 ]
[ 10394-40-8 ]

Reference： [1] Journal of Pharmacy and Pharmacology, 1949, vol. 1, p. 957,968

8
[ 614-97-1 ]
[ 77-78-1 ]
[ 10394-40-8 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 1143,1153

9
[ 50-00-0 ]
[ 496-72-0 ]
[ 10394-40-8 ]

Reference： [1] Chemische Berichte, 1892, vol. 25, p. 2711

10
[ 614-97-1 ]
[ 77-78-1 ]
[ 10394-40-8 ]
[ 10394-35-1 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 1143,1153

11
[ 7647-01-0 ]
[ 50-00-0 ]
[ 496-72-0 ]
[ 10394-40-8 ]

Reference： [1] Chemische Berichte, 1892, vol. 25, p. 2711
[2] Chemische Berichte, 1893, vol. 26, p. 190[3] Chemische Berichte, 1894, vol. 27, p. 2776

12
[ 10394-40-8 ]
[ 53484-18-7 ]

Reference： [1] Patent: US4977175, 1990, A,

[ 10394-40-8 ] Synthesis Path-Downstream 1~28

1
[ 614-97-1 ]
[ 77-78-1 ]
[ 10394-40-8 ]

Reference： [1]Journal of the Chemical Society,1931,p. 1143,1153

2
[ 614-97-1 ]
[ 77-78-1 ]
[ 10394-40-8 ]
[ 10394-35-1 ]

Reference： [1]Journal of the Chemical Society,1931,p. 1143,1153

3
[ 50-00-0 ]
[ 496-72-0 ]
[ 10394-40-8 ]

Reference： [1]Chemische Berichte,1892,vol. 25,p. 2711

4
[ 65081-42-7 ]
[ 10394-40-8 ]

Reference： [1]Journal of Pharmacy and Pharmacology,1949,vol. 1,p. 957,968

5
[ 10394-40-8 ]
[ 937-14-4 ]
3-Chloro-benzoic acid 5-hydroxy-1,6-dimethyl-1H-benzoimidazol-2-yl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 625 - 630

7
[ 7647-01-0 ]
[ 50-00-0 ]
[ 496-72-0 ]
[ 10394-40-8 ]

Reference： [1]Chemische Berichte,1892,vol. 25,p. 2711

8
[ 10394-40-8 ]
[ 53484-18-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium permanganate;	STR44 An aqueous solution (100 ml) of 3.95 g of <strong>[10394-40-8]1,6-dimethylbenzimidazole</strong> and 10 g of potassium permanganate was stirred at 50 C. for 2 hours and 2 g of potassium permanganate was further added to the mixture. The mixture was stirred at 80 C. for further 2 hours. After insoluble matters were filtered off, the filtrate was rendered pH 4 with 1 N hydrochloric acid and concentrated under reduced pressure to give 7.33 g of 1-methylbenzimidazole-6-carboxylic acid as the mixture with potassium chloride. The above compound was heated to reflux in 150 ml of methanol overnight in the presence of 3 ml of conc. sulfuric acid. The reaction solution was concentrated under reduced pressure and water was added to the concentrate.

Reference： [1]Patent: US4977175,1990,A

9
aqueous potassium carbonate [ No CAS ]
ethyl acetate n-hexane [ No CAS ]
[ 131019-87-9 ]
[ 10394-40-8 ]

Yield	Reaction Conditions	Operation in experiment
4.01 g (57%)	With formic acid; In hydrogenchloride; water;	STR43 A mixture of 6.60 g of <strong>[131019-87-9]1-amino-4-methyl-2-(N-methylamino)benzene</strong> and a solution of 3.5 ml of formic acid in 50 ml of a 4N HCl was stirred at 100 C. for 3.5 hours. The reaction solution was concentrated under reduced pressure and water was added to the residue. After washing with ethyl acetate, the aqueous phase was rendered alkaline with aqueous potassium carbonate followed by extraction with chloroform. The chloroform layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (40 g). Elution with ethyl acetate followed by recyrstallization from ethyl acetate-hexane gave 4.01 g (57%) of 1,6-dimethylbenzimidazole.

Reference： [1]Patent: US4977175,1990,A

10
[ 67-56-1 ]
[ 89-62-3 ]
[ 10394-40-8 ]
[ 10394-35-1 ]
[ 614-97-1 ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 5172 - 5181

11
[ 67-56-1 ]
[ 496-72-0 ]
[ 10394-40-8 ]
[ 10394-35-1 ]
[ 614-97-1 ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 5172 - 5181

12
[ 10394-40-8 ]
[ 119-61-9 ]
(1,6-dimethylbenzimidazol-2-yl)-diphenyl-methanol [ No CAS ]