1H-Benzimidazol-2-amine,6-chloro- supplier

Name
6-CHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE
EINECS
CAS No. 5418-93-9
Article Data22
CAS DataBase
Density 1.533 g/cm³
Solubility
Melting Point 167-168 °C
Formula C₇H₆ClN₃
Boiling Point 402.5 °C at 760 mmHg
Molecular Weight 167.598
Flash Point 197.3 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1H-Benzimidazol-2-amine,5-chloro- (9CI);Benzimidazole, 2-amino-5(or 6)-chloro- (7CI);Benzimidazole,2-amino-5-chloro- (8CI);2-Amino-5-chloro-1H-benzimidazole;2-Amino-5-chlorobenzimidazole;2-Amino-6-chlorobenzimidazole;5-Chloro-2-aminobenzimidazole;5-Chloro-2-benzimidazolamine;5-Chlorobenzoimidazol-2-ylamine;NSC 10545;
PSA 54.70000
LogP 2.37970

Synthetic route

: 1184-90-3
aminoiminomethanesulfonic acid

: 95-83-0
4-Chloro-1,2-phenylenediamine

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

Conditions

Conditions	Yield
at 60℃;	97%

: 506-68-3
bromocyane

: 95-83-0
4-Chloro-1,2-phenylenediamine

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

Conditions

Conditions	Yield
In ethanol; water at 70℃; for 1h;	87%
In methanol; water at 50℃; for 1h;	82%
With water

: 934-32-7
1H-benzimidazol-2-amine

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

Conditions

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In water at 20℃; for 1.5h;	72%
With hydrogenchloride; dihydrogen peroxide In water at 20℃; for 1.5h;	72%
With hydrogenchloride; water; dihydrogen peroxide

: 506-68-3
bromocyane

: 95-83-0
4-Chloro-1,2-phenylenediamine

A: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

B: 5418-93-9
6-chloro-1H-benzoimidazol-2-amine

Conditions

Conditions	Yield
In methanol; water at 60℃; for 3h; Sealed tube;

...Expand

: 1635-61-6
5-chloro-2-nitroaniline

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(ll) chloride / ethyl acetate; ethanol / 16 h / 80 °C 2: 70 °C View Scheme

: 89-63-4
4-Chloro-2-nitroaniline

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: iron; ammonium chloride / ethanol; water / 1 h / 90 °C 2: 70 °C View Scheme

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

Polymer, oxidized, degree of functionalization: -CHO 2.607 mmole/g, -CH2Cl 0.258 mmole/g; Monomer(s): chloromethylated styrene 93 percent; divinylbenzene 7 percent: Polymer, oxidized, degree of functionalization: -CHO 2.607 mmole/g, -CH2Cl 0.258 mmole/g; Monomer(s): chloromethylated styrene 93 percent; divinylbenzene 7 percent

Polymer, oxidized, grafted by 2-amino-5(6)-chlorobenzimidazole, degree of functionalization: -CH=N-Het 1,661 mmol/g, -CHO 0.300 mmole/g, -CH2Cl 0.195 mmole/g; Monomer(s): chloromethylated styrene 93 percent; divinylbenzene 7 percent: Polymer, oxidized, grafted by 2-amino-5(6)-chlorobenzimidazole, degree of functionalization: -CH=N-Het 1,661 mmol/g, -CHO 0.300 mmole/g, -CH2Cl 0.195 mmole/g; Monomer(s): chloromethylated styrene 93 percent; divinylbenzene 7 percent

Conditions

Conditions	Yield
condensation;	84.76%

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 219635-54-8
3β-acetoxy-16-formyl-17-acetamido-androst-5,16-diene

: 3β-acetoxy-6'-chloroandrost[16,17-e]benzimidazolo[1’,2’-a]pyrimidin-5-ene

Conditions

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide at 110℃; for 5h; Inert atmosphere;	82%

: 100-48-1
pyridine-4-carbonitrile

: 683-08-9
Diethyl methylphosphonate

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 446-52-6
2-Fluorobenzaldehyde

: 7-chloro-2-(2-fluoro-phenyl)-4-pyridin-4-yl-benzo[4,5]imidazo[1,2-a]pyrimidine

Conditions

Conditions	Yield
Stage #1: pyridine-4-carbonitrile; Diethyl methylphosphonate With n-butyllithium In tetrahydrofuran; hexane at -78 - -50℃; for 0.5h; Stage #2: 2-Fluorobenzaldehyde In tetrahydrofuran; hexane at -50 - 0℃; for 0.75h; Stage #3: 5-chloro-1H-benzo[d]imidazol-2-amine In tetrahydrofuran; N,N-dimethyl-formamide for 8h; Heating;	76%

...Expand

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 624-83-9
methyl isocyanate

: 84388-89-6
2-Amino-5-chloro-benzoimidazole-1-carboxylic acid methylamide

Conditions

Conditions	Yield
In acetone at -30℃; for 4h;	70%

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 886-38-4
diphenylcyclopropenone

: (3R,4S)-8-Chloro-3,4-diphenyl-3,4-dihydro-1H-benzo[4,5]imidazo[1,2-a]pyrimidin-2-one

: (3R,4S)-7-Chloro-3,4-diphenyl-3,4-dihydro-1H-benzo[4,5]imidazo[1,2-a]pyrimidin-2-one

: (3S,4S)-7-Chloro-3,4-diphenyl-3,4-dihydro-1H-benzo[4,5]imidazo[1,2-a]pyrimidin-2-one

Conditions

Conditions	Yield
In tetrahydrofuran for 48h; Ambient temperature;	A 50% B 10% C 12%

...Expand

: 2-bromo-1-(2,3-dichlorophenyl)ethanone

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A: 1616405-92-5
2-(2-amino-6-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanol

B: 1616406-38-2
2-(2-amino-5-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanol

Conditions

Conditions	Yield
Stage #1: 2-bromo-1-(2,3-dichlorophenyl)ethanone; 5-chloro-1H-benzo[d]imidazol-2-amine With potassium hydroxide In acetone at 20℃; for 0.416667h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 1h; Inert atmosphere;	A 39.8% B 39.8%

...Expand

: 979-02-2
16-dehydropregnenolone acetate

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A: 3β-acetoxy-17aα-(6'-chlorobenzimidazol-2'-yl-amino)-16α,1'-cyclo-17aβ-methyl-D-homoandrost-5-en-17-one

B: 3β-acetoxy-9'-chloro-4'-methylandrost-5-eno[16,17-e]benzimidazole[1,2-a]pyrimidine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 140℃; for 16h; Solvent; Reagent/catalyst; Temperature; Reflux;	A 11% B n/a

...Expand

: 979-02-2
16-dehydropregnenolone acetate

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A: 3β-acetoxy-17aα-(5'-chlorobenzimidazol-2'-yl-amino)-16α,1'-cyclo-17aβ-methyl-D-homoandrost-5-en-17-one

B: 3β-acetoxy-8'-chloro-4'-methylandrost-5-eno[16,17-e]benzimidazole[1,2-a]pyrimidine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 140℃; for 16h; Solvent; Reagent/catalyst; Temperature; Reflux;	A 11% B n/a

...Expand

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 121-51-7
3-nitrobenzenesulphonyl chloride

: 5-chloro-1-(3-nitro-benzenesulfonyl)-1H-benzimidazol-2-ylamine

Conditions

Conditions	Yield
With pyridine

: 39075-92-8
3,5-dibromo-2-hydroxy-benzoyl chloride

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 78417-58-0
3,5-Dibromo-N-(5-chloro-1H-benzoimidazol-2-yl)-2-hydroxy-benzamide

Conditions

Conditions	Yield
In chlorobenzene for 3h; Heating;

: 108-24-7
acetic anhydride

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A: 90964-27-5
1-(2-Amino-6-chloro-benzoimidazol-1-yl)-ethanone

B: 90964-26-4
1-(2-Amino-5-chloro-benzoimidazol-1-yl)-ethanone

Conditions

Conditions	Yield
In acetone at -35℃; Title compound not separated from byproducts;

...Expand

: 108-24-7
acetic anhydride

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 35642-74-1
N-(5-chloro-1(3)H-benzoimidazol-2-yl)-acetamide

Conditions

Conditions	Yield
1.) -35 deg C, acetone, 2.) 1 h, 100 deg C, pyridine; Yield given. Multistep reaction;

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 1122-85-6
phenyl cyanate

: 2-Amino-5-chloro-benzoimidazole-1-carboximidic acid phenyl ester

Conditions

Conditions	Yield
In 1,4-dioxane; water at 25℃; Rate constant;

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 121-92-6
3-nitrobenzoic acid

: N-(5-chloro-1H-benzoimidazol-2-yl)-3-nitro-benzamide

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide

: 527-69-5
2-furancarbonyl chloride

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A 5-Chloro-2-(2'-furoyl)aminobenzimidazole: 5-Chloro-2-(2'-furoyl)aminobenzimidazole

B: 2-(2-furanacrylyl)aminobenzimidazole

Conditions

Conditions	Yield
With acetic acid In pyridine; water

...Expand

: 15851-87-3
5-(4-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A: 7-chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-4-one

B: 1221962-62-4
7-Chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]-benz-imidazol-4-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 0.166667h; Heating; Reflux;

...Expand

: 15851-87-3
5-(4-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A: 1221962-62-4
7-Chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]-benz-imidazol-4-one

B: 1221962-61-3
6-chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-4-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 0.166667h; Reflux;

...Expand

: 15851-87-3
5-(4-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 1221962-60-2
3-amino-N-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)propanoic acid hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 0.17 h / Reflux 2: hydrogenchloride; acetic acid / 1.5 h / Reflux View Scheme

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 150454-07-2
5-chloro-2-aminobenzimidazole hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water

: 344287-60-1
2,2-difluoro-3-phenylcyclopropane-1-carboxylic acid

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 1422435-47-9
2,2-difluoro3-phenylcyclopropanecarboxylic acid (5-chloro-1H-benzoimidazol-2-yl)amide

Conditions

Conditions	Yield
Stage #1: 2,2-difluoro-3-phenylcyclopropane-1-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 5-chloro-1H-benzo[d]imidazol-2-amine In N,N-dimethyl-formamide at 20℃; for 16h;	57 mg

: 2-bromo-1-(2,3-dichlorophenyl)ethanone

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

A: 1616406-36-0
2-(2-amino-5-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanone

B

Conditions

Conditions	Yield
With potassium hydroxide In acetone at 20℃; for 0.416667h; Inert atmosphere; Overall yield = 23.63 %; Overall yield = 0.150 g;

...Expand

4-chlorobenzaldehyde: 4-chlorobenzaldehyde

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 8-chloro-2,4-bis(4-chlorophenyl)benzo[4,5]imidazo[1,2-a]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide / acetonitrile / 0.17 h / 20 °C / Inert atmosphere 2: silver carbonate / acetonitrile / 81 - 83 °C / Inert atmosphere View Scheme

...Expand

: 873-73-4
4-n-chlorophenylacetylene

: 104-88-1
4-chlorobenzaldehyde

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: C22H14Cl3N3

Conditions

Conditions	Yield
With copper(l) iodide In acetonitrile at 20℃; for 0.166667h; Inert atmosphere;

...Expand

: 873-73-4
4-n-chlorophenylacetylene

: 100-52-7
benzaldehyde

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 8-chloro-4-(4-chlorophenyl)-2-phenylbenzo[4,5]imidazo[1,2-a]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide / acetonitrile / 0.17 h / 20 °C / Inert atmosphere 2: silver carbonate / acetonitrile / 81 - 83 °C / Inert atmosphere View Scheme

...Expand

: 873-73-4
4-n-chlorophenylacetylene

: 100-52-7
benzaldehyde

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: C22H15Cl2N3

Conditions

Conditions	Yield
With copper(l) iodide In acetonitrile at 20℃; for 0.166667h; Inert atmosphere;

...Expand

: (S)-1-(tetrahydropyran-4-yl)pyrrolidine-2-carboxylic acid

: 5418-93-9
5-chloro-1H-benzo[d]imidazol-2-amine

: 1234316-59-6
(S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid (5-chloro-1H-benzimidazol-2-yl)-amide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane

1H-Benzimidazol-2-amine,6-chloro- Specification

The 1H-Benzimidazol-2-amine,6-chloro-, with the CAS registry number 5418-93-9, is also known as 2-Amino-6-chlorobenzimidazole. It belongs to the product categories of Benzimidazole; Pharmacetical; Imidazol & Benzimidazole. This chemical's molecular formula is C₇H₆ClN₃ and molecular weight is 167.6. Its IUPAC name is called 6-chloro-1H-benzimidazol-2-amine.

Physical properties of 1H-Benzimidazol-2-amine,6-chloro-: (1)ACD/LogP: 1.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.86; (4)ACD/LogD (pH 7.4): 1.82; (5)ACD/BCF (pH 5.5): 1.52; (6)ACD/BCF (pH 7.4): 13.95; (7)ACD/KOC (pH 5.5): 24.19; (8)ACD/KOC (pH 7.4): 222.03; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)Index of Refraction: 1.777; (12)Molar Refractivity: 45.75 cm³; (13)Molar Volume: 109.3 cm³; (14)Surface Tension: 79.6 dyne/cm; (15)Density: 1.533 g/cm³; (16)Flash Point: 197.3 °C; (17)Enthalpy of Vaporization: 65.37 kJ/mol; (18)Boiling Point: 402.5 °C at 760 mmHg; (19)Vapour Pressure: 1.09E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC2=C(C=C1Cl)NC(=N2)N
(2)InChI: InChI=1S/C7H6ClN3/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H3,9,10,11)
(3)InChIKey: PDOCNPCPPLPXRV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	112mg/kg (112mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#12521,

Product Name

6-CHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE

Synthetic route

1H-Benzimidazol-2-amine,6-chloro- Specification

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