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934-22-5

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934-22-5 Usage

General Description

1H-Benzimidazol-5-ylamine, also known as 5-Aminobenzimidazole, is an organic compound with the formula C7H7N3. It is a heterocyclic aromatic amine containing both an imidazole and an aniline functional group. This chemical is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and dyes. It has also been studied for its potential as an anti-cancer agent. 1H-Benzimidazol-5-ylamine is a white to off-white crystalline solid at room temperature and is soluble in polar organic solvents such as ethanol and dimethyl sulfoxide, while being only sparingly soluble in water. It is important to handle this chemical with caution as it can cause skin and eye irritation, and proper safety measures should be taken when working with it.

Check Digit Verification of cas no

The CAS Registry Mumber 934-22-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 4 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 934-22:
(5*9)+(4*3)+(3*4)+(2*2)+(1*2)=75
75 % 10 = 5
So 934-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H7N3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,8H2,(H,9,10)

934-22-5 Well-known Company Product Price

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  • Aldrich

  • (725005)  6-Aminobenzimidazole  95%

  • 934-22-5

  • 725005-500MG

  • 726.57CNY

  • Detail

934-22-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1H-1,3-Benzimidazol-5-amine

1.2 Other means of identification

Product number -
Other names 1H-BENZOIMIDAZOL-5-YLAMINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:934-22-5 SDS

934-22-5Synthetic route

5-nitrobenzimidazole
94-52-0

5-nitrobenzimidazole

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol under 760.051 Torr; for 20h;100%
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran; ethanol at 20℃; for 4h;92%
With [Co(κS,N-4-(trifluoromethyl)pyrimidine-2-thiolate)3]; methylhydrazine In methanol at 70℃; for 18h; Sealed tube;86%
formic acid
64-18-6

formic acid

benzene-1,2,4-triamine
615-71-4

benzene-1,2,4-triamine

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride In water; toluene at 160℃; for 0.166667h; Microwave irradiation;81%
With chloro-trimethyl-silane In water; N,N-dimethyl-formamide at 120℃; for 0.166667h; Microwave irradiation;81%
Behandeln der entstandenen Formylverbindung mit siedender verduennter Schwefelsaeure;
anschliessend Behandeln mit verd.Schwefelsaeue;
formic acid
64-18-6

formic acid

benzene-1,2,4-triyltriamine trihydrochloride

benzene-1,2,4-triyltriamine trihydrochloride

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

Conditions
ConditionsYield
With phosphoric acid; water
4-Nitrophenylene-1,2-diamine
99-56-9

4-Nitrophenylene-1,2-diamine

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 24 h / Reflux
2: palladium on activated charcoal; hydrazine hydrate / ethanol / 4 h / Reflux
View Scheme
benzoimidazole
51-17-2

benzoimidazole

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; potassium nitrate / 2.08 h / 0 °C
2: tin(II) chloride dihdyrate / ethyl acetate / 12 h / Reflux
View Scheme
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 8 h / Reflux
2: sulfuric acid; potassium nitrate / 2.08 h / 0 °C
3: tin(II) chloride dihdyrate / ethyl acetate / 12 h / Reflux
View Scheme
3,4-dimethoxyphenylisocyanate
37527-66-5

3,4-dimethoxyphenylisocyanate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

1-(1H-benzo[d]imidazol-5-yl)-3-(3,4-dimethoxyphenyl)urea
1070654-59-9

1-(1H-benzo[d]imidazol-5-yl)-3-(3,4-dimethoxyphenyl)urea

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Heating / reflux;98%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

3,4-diethoxy-3-cyclobuten-1,2-dione
5231-87-8

3,4-diethoxy-3-cyclobuten-1,2-dione

3-(1H-benzimidazol-5-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione
922736-19-4

3-(1H-benzimidazol-5-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione

Conditions
ConditionsYield
In ethanol at 75℃; for 20h;97%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

4-(thiazol-2-yl)-benzaldehyde
198904-53-9

4-(thiazol-2-yl)-benzaldehyde

(1H-benzimidazol-5-ylamino)[4-(1,3-thiazol-2-yl)phenyl]acetonitrile

(1H-benzimidazol-5-ylamino)[4-(1,3-thiazol-2-yl)phenyl]acetonitrile

Conditions
ConditionsYield
Stage #1: 5-aminobenzimidazole; 4-(thiazol-2-yl)-benzaldehyde With acetic acid at 20℃; for 0.333333h;
Stage #2: trimethylsilyl cyanide at 20℃; for 2h;
96%
Stage #1: 5-aminobenzimidazole; 4-(thiazol-2-yl)-benzaldehyde With acetic acid at 20℃; for 0.333333h;
Stage #2: trimethylsilyl cyanide for 2h;
96%
2,4-dichloro-5-bromopyrimidine
36082-50-5

2,4-dichloro-5-bromopyrimidine

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

(1H-Benzoimidazol-5-yl)-(5-bromo-2-chloro-pyrimidin-4-yl)-amine
852357-08-5

(1H-Benzoimidazol-5-yl)-(5-bromo-2-chloro-pyrimidin-4-yl)-amine

Conditions
ConditionsYield
With sodium carbonate In ethanol at 20℃; for 24h;93%
With sodium carbonate In ethanol at 20℃; for 16h;
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

3,5-dimethoxybenzaldehdye
7311-34-4

3,5-dimethoxybenzaldehdye

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

tert-butyl 11-(3,5-dimethoxyphenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-28-8

tert-butyl 11-(3,5-dimethoxyphenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 14h; regioselective reaction;90%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

tert-butyl 11-(3-methoxyphenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-29-9

tert-butyl 11-(3-methoxyphenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 12h; regioselective reaction;90%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

tert-butyl 11-(2-chlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-26-6

tert-butyl 11-(2-chlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 9h; regioselective reaction;89%
2-bromo-4-fluorobenzaldehyde
59142-68-6

2-bromo-4-fluorobenzaldehyde

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

3-fluoro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

3-fluoro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 12h; Reflux;89%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

11-(2-bromophenyl)-8,8-dimethyl-6a,7,8,9,10a,11-hexahydro-1H-imidazo[4,5-a]acridin-10(6H)-one

11-(2-bromophenyl)-8,8-dimethyl-6a,7,8,9,10a,11-hexahydro-1H-imidazo[4,5-a]acridin-10(6H)-one

Conditions
ConditionsYield
In 1,4-dioxane Reflux;87%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

1-methyl-6-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

1-methyl-6-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

N-(1H-benzo[d]imidazol-5-yl)-1-methyl-6-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide

N-(1H-benzo[d]imidazol-5-yl)-1-methyl-6-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;87%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

tert-butyl 11-(4-chlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-22-2

tert-butyl 11-(4-chlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 12h; regioselective reaction;86%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

11-(3,4-dichlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-27-7

11-(3,4-dichlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 10h; regioselective reaction;86%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

piperonal
120-57-0

piperonal

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

tert-butyl 11-piperonyl-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-30-2

tert-butyl 11-piperonyl-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 15h; regioselective reaction;86%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 15h; Reagent/catalyst; Solvent; Reflux;86%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

2-bromo-5-fluorobenzaldehyde
94569-84-3

2-bromo-5-fluorobenzaldehyde

2-fluoro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

2-fluoro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 12h; Reflux;86%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

tert-butyl 11-(3-chlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-25-5

tert-butyl 11-(3-chlorophenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 13h; regioselective reaction;85%
2-bromo-5-methoxy-benzaldehyde
7507-86-0

2-bromo-5-methoxy-benzaldehyde

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

2-methoxy-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

2-methoxy-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 18h; Reflux;85%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

5-chloro-1-methyl-1H-imidazole-2-carbaldehyde
37050-18-3

5-chloro-1-methyl-1H-imidazole-2-carbaldehyde

N-((5-chloro-1-methyl-1H-imidazol-2-yl)methyl)-1H-benzo[d]-imidazol-5-amine

N-((5-chloro-1-methyl-1H-imidazol-2-yl)methyl)-1H-benzo[d]-imidazol-5-amine

Conditions
ConditionsYield
Stage #1: 5-aminobenzimidazole; 5-chloro-1-methyl-1H-imidazole-2-carbaldehyde In methanol at 60℃; for 16h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 2h;
85%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

2-chloro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

2-chloro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 12h; Reflux;84%
2-bromo-4-fluorobenzaldehyde
59142-68-6

2-bromo-4-fluorobenzaldehyde

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

3-fluoro-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

3-fluoro-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 14h; Reflux;84%
2-bromothiophene-3-carbaldehyde
1860-99-7

2-bromothiophene-3-carbaldehyde

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

11,11-dimethyl-11,12-dihydroimidazo[4,5,1-ij]quinolino[4,3,2-de]thieno[3,2-b]quinolin-13(10H)-one

11,11-dimethyl-11,12-dihydroimidazo[4,5,1-ij]quinolino[4,3,2-de]thieno[3,2-b]quinolin-13(10H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 16h; Reflux;84%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

tert-butyl 11-(2,4-dichlorophenyl)-10-oxo-7,8,10,11-tetrahydro-1H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-31-3

tert-butyl 11-(2,4-dichlorophenyl)-10-oxo-7,8,10,11-tetrahydro-1H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 9h; regioselective reaction;83%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 16h; Reflux;83%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

5-methylcyclohexan-1,3-dione
4341-24-6

5-methylcyclohexan-1,3-dione

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

2-chloro-12-methyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

2-chloro-12-methyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 12h; Reflux;83%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

2-chloro-5-nitrobenzaldehyde
6361-21-3

2-chloro-5-nitrobenzaldehyde

12,12-dimethyl-2-nitro-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

12,12-dimethyl-2-nitro-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 10h; Reflux;83%
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

tert-butyl 11-(2-methoxyphenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate
1431468-32-4

tert-butyl 11-(2-methoxyphenyl)-10-oxo-7,8,10,11-tetrahydro-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine-9(6H)-carboxylate

Conditions
ConditionsYield
In ethanol at 80℃; for 12h; regioselective reaction;82%
5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

dimedone
126-81-8

dimedone

2-bromo-4-chlorobenzaldehyde
84459-33-6

2-bromo-4-chlorobenzaldehyde

3-chloro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

3-chloro-12,12-dimethyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 12h; Reflux;82%
5-methylcyclohexan-1,3-dione
4341-24-6

5-methylcyclohexan-1,3-dione

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

2-bromo-4-chlorobenzaldehyde
84459-33-6

2-bromo-4-chlorobenzaldehyde

3-chloro-12-methyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

3-chloro-12-methyl-12,13-dihydroimidazo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; L-proline In 1,4-dioxane for 12h; Reflux;82%
C18H14Cl2N4

C18H14Cl2N4

5-aminobenzimidazole
934-22-5

5-aminobenzimidazole

N4-(2-(1H-indol-3-yl)ethyl)-N2-(1H-benzo[d]imidazol-5-yl)-6-chloroquinazoline-2,4-diamine

N4-(2-(1H-indol-3-yl)ethyl)-N2-(1H-benzo[d]imidazol-5-yl)-6-chloroquinazoline-2,4-diamine

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 120℃; for 6h;82%

934-22-5Downstream Products

934-22-5Relevant articles and documents

5,5′-Dibenzoimidazole as building block for a new 3D Co(II) coordination polymer: A combined EPR and DFT study using UB3LYP model

Datta, Amitabha,Massera, Chiara,Garribba, Eugenio,Frontera, Antonio

, p. 473 - 479 (2019)

A new Co(II) three-dimensional coordination polymer, [Co(L)(L′)]n (1) [where L = 5,5′-dibenzoimidazole, and L′ = doubly deprotonated terephthalic acid] has been synthesized hydro(solvo)thermally and its molecular and crystal structure have been elucidated through single crystal X-ray diffraction analysis. Each Co(II) ion displays a slightly distorted trigonal bipyramidal geometry, the apical positions being occupied by the nitrogen atoms of two symmetry-related dibenzoimidazole ligands, while the oxygen atoms from three distinct terephthalic acids are in the equatorial plane. Considering the Co2C2O6 dimeric moieties as nodes, and the ancillary ligands as connectors, the structure can be simplified as a 8-c uninodal net of the type bcu, body centered cubic, with point symbol {424·64} and vertex symbol [4·4·4·4·4·4·4·4·4·4·4·4·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·*·*·*·*]. The EPR spectra for 1 have been reported, showing g|| = 2.176 and g⊥ = 2.052 at RT (room temperature), and g|| = 2.172 and g⊥ = 2.060 at LNT (liquid nitrogen temperature). Finally, the electronic nature of the molecular geometry of 1 has been explored by DFT computation applying the UB3LYP/def2-TZVP level of theory, showing the energy difference between the high spin and low spin configurations.

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.

, p. 2895 - 2906 (2021/02/27)

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

Homology modelling, molecular dynamics simulation and docking evaluation of β-tubulin of Schistosoma mansoni

El-Shehabi, Fouad,Mansour, Basem,Bayoumi, Waleed A.,El Bialy, Serry A.,Elmorsy, Mohammad A.,Eisa, Hassan M.,Taman, Amira

, (2021/09/16)

Schistosomiasis is one of the neglected diseases causing considerable morbidity and mortality throughout the world. Microtubules with its main component, tubulin play a vital role in helminthes including schistosomes. Benzimidazoles represent potential drug candidates by binding β-tubulin. The study aimed to generate a homology model for the β-tubulin of S. mansoni using the crystal structure of O vis aries (Sheep) β-tubulin (PDB ID: 3N2G D) as a template, then different β-tubulin models were generated and two previously reported benzimidazole derivatives (NBTP-F and NBTP-OH) were docked to the generated models, the binding results indicated that both S. mansoni, S. haematobium were susceptible to the two NBTP derivatives. Additionally, three mutated versions of S. mansoni β-tubulin wild-type were generated and the mutation (F185Y) seems to slightly enhance the ligand binding. Dynamics simulation experiments showed S. haematobium β-tubulin is highly susceptible to the tested compounds; similar to S. mansoni, moreover, mutated models of S. mansoni β-tubulin altered its NBTPs susceptibility. Moreover, additional seven new benzimidazole derivatives were synthesized and tested by molecular docking on the generated model binding site of S. mansoni β-tubulin and were found to have good interaction inside the pocket.

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