5418-93-9

Basic information

• Product Name: 6-CHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE
• Synonyms: 2-amino-5-chloro-benzimidazol;5-chloro-1h-benzimidazol-2-amin;5-CHLORO-1H-BENZOIMIDAZOL-2-YLAMINE;5-CHLORO-1H-BENZIMIDAZOLE-2-AMINE;5-CHLORO-1H-BENZIMIDAZOL-2-AMINE;6-CHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE;2-AMINO-6-CHLOROBENZIMIDAZOLE;1H-Benzimidazol-2-amine,5-chloro-(9CI)
• CAS NO: 5418-93-9
• Molecular Formula: C₇H₆ClN₃
• Molecular Weight: 167.6
• Product Categories: BENZIMIDAZOLE;pharmacetical;Imidazol&Benzimidazole
• Mol File: 5418-93-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 167-168 °C
• Boiling Point: 276.48°C (rough estimate)
• Flash Point: 197.3 °C
• Appearance: /
• Density: 1.3144 (rough estimate)
• Vapor Pressure: 1.09E-06mmHg at 25°C
• Refractive Index: 1.6010 (estimate)
• Storage Temp.: 2-8°C
• PKA: 10.16±0.10(Predicted)
• CAS DataBase Reference: 6-CHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE(5418-93-9)
• EPA Substance Registry System: 6-CHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE(5418-93-9)

Safety Data

• Hazardous Substances Data: 5418-93-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2459, 1947 DOI: 10.1021/ja01202a062

InChI:InChI=1/C7H6ClN3/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H3,9,10,11)

Synthetic route

aminoiminomethanesulfonic acid (1184-90-3) + 4-Chloro-1,2-phenylenediamine (95-83-0) → 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9)

Conditions	Yield
at 60℃;	97%

bromocyane (506-68-3) + 4-Chloro-1,2-phenylenediamine (95-83-0) → 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9)

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

1H-benzimidazol-2-amine (934-32-7) → 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9)

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

bromocyane (506-68-3) + 4-Chloro-1,2-phenylenediamine (95-83-0) → 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + 6-chloro-1H-benzoimidazol-2-amine (5418-93-9)

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

5-chloro-2-nitroaniline (1635-61-6) → 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9)

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

4-Chloro-2-nitroaniline (89-63-4) → 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9)

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

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + 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

Conditions	Yield
condensation;	84.76%

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + 3β-acetoxy-16-formyl-17-acetamido-androst-5,16-diene (219635-54-8) → 3β-acetoxy-6'-chloroandrost[16,17-e]benzimidazolo[1’,2’-a]pyrimidin-5-ene

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

pyridine-4-carbonitrile (100-48-1) + Diethyl methylphosphonate (683-08-9) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + 2-Fluorobenzaldehyde (446-52-6) → 7-chloro-2-(2-fluoro-phenyl)-4-pyridin-4-yl-benzo[4,5]imidazo[1,2-a]pyrimidine

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%

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + methyl isocyanate (624-83-9) → 2-Amino-5-chloro-benzoimidazole-1-carboxylic acid methylamide (84388-89-6)

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

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + diphenylcyclopropenone (886-38-4) → (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	Yield
In tetrahydrofuran for 48h; Ambient temperature;	A 50% B 10% C 12%

2-bromo-1-(2,3-dichlorophenyl)ethanone + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 2-(2-amino-6-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanol (1616405-92-5) + 2-(2-amino-5-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanol (1616406-38-2)

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%

16-dehydropregnenolone acetate (979-02-2) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 3β-acetoxy-17aα-(6'-chlorobenzimidazol-2'-yl-amino)-16α,1'-cyclo-17aβ-methyl-D-homoandrost-5-en-17-one + 3β-acetoxy-9'-chloro-4'-methylandrost-5-eno[16,17-e]benzimidazole[1,2-a]pyrimidine

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

16-dehydropregnenolone acetate (979-02-2) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 3β-acetoxy-17aα-(5'-chlorobenzimidazol-2'-yl-amino)-16α,1'-cyclo-17aβ-methyl-D-homoandrost-5-en-17-one + 3β-acetoxy-8'-chloro-4'-methylandrost-5-eno[16,17-e]benzimidazole[1,2-a]pyrimidine

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

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + 3-nitrobenzenesulphonyl chloride (121-51-7) → 5-chloro-1-(3-nitro-benzenesulfonyl)-1H-benzimidazol-2-ylamine

Conditions	Yield
With pyridine

3,5-dibromo-2-hydroxy-benzoyl chloride (39075-92-8) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 3,5-Dibromo-N-(5-chloro-1H-benzoimidazol-2-yl)-2-hydroxy-benzamide (78417-58-0)

Conditions	Yield
In chlorobenzene for 3h; Heating;

acetic anhydride (108-24-7) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 1-(2-Amino-6-chloro-benzoimidazol-1-yl)-ethanone (90964-27-5) + 1-(2-Amino-5-chloro-benzoimidazol-1-yl)-ethanone (90964-26-4)

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

acetic anhydride (108-24-7) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → N-(5-chloro-1(3)H-benzoimidazol-2-yl)-acetamide (35642-74-1)

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

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + phenyl cyanate (1122-85-6) → 2-Amino-5-chloro-benzoimidazole-1-carboximidic acid phenyl ester

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

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) + 3-nitrobenzoic acid (121-92-6) → N-(5-chloro-1H-benzoimidazol-2-yl)-3-nitro-benzamide

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

2-furancarbonyl chloride (527-69-5) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 5-Chloro-2-(2'-furoyl)aminobenzimidazole + 2-(2-furanacrylyl)aminobenzimidazole

Conditions	Yield
With acetic acid In pyridine; water

5-(4-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (15851-87-3) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 7-chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-4-one + 7-Chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]-benz-imidazol-4-one (1221962-62-4)

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

5-(4-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (15851-87-3) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 7-Chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]-benz-imidazol-4-one (1221962-62-4) + 6-chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-4-one (1221962-61-3)

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

5-(4-chlorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (15851-87-3) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 3-amino-N-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)propanoic acid hydrochloride (1221962-60-2)

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

5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 5-chloro-2-aminobenzimidazole hydrochloride (150454-07-2)

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

2,2-difluoro-3-phenylcyclopropane-1-carboxylic acid (344287-60-1) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 2,2-difluoro3-phenylcyclopropanecarboxylic acid (5-chloro-1H-benzoimidazol-2-yl)amide (1422435-47-9)

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 + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 2-(2-amino-5-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanone (1616406-36-0)

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

+ 4-chlorobenzaldehyde + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 8-chloro-2,4-bis(4-chlorophenyl)benzo[4,5]imidazo[1,2-a]pyrimidine

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

4-n-chlorophenylacetylene (873-73-4) + 4-chlorobenzaldehyde (104-88-1) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → C22H14Cl3N3

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

4-n-chlorophenylacetylene (873-73-4) + benzaldehyde (100-52-7) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → 8-chloro-4-(4-chlorophenyl)-2-phenylbenzo[4,5]imidazo[1,2-a]pyrimidine

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

4-n-chlorophenylacetylene (873-73-4) + benzaldehyde (100-52-7) + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → C22H15Cl2N3

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

(S)-1-(tetrahydropyran-4-yl)pyrrolidine-2-carboxylic acid + 5-chloro-1H-benzo[d]imidazol-2-amine (5418-93-9) → (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid (5-chloro-1H-benzimidazol-2-yl)-amide (1234316-59-6)

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

Upstream product

• 4887-95-0 2,6-dichloro-1H-1,3-benzimidazole 
• 506-68-3 bromocyane 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 89-63-4 4-Chloro-2-nitroaniline 
• 1635-61-6 5-chloro-2-nitroaniline 
• 1184-90-3 aminoiminomethanesulfonic acid 
• 934-32-7 1H-benzimidazol-2-amine 

Downstream Products

• 1388031-41-1 2-bromo-5-chloro-1H-benzo[d]imidazole 
• 1616406-36-0 2-(2-amino-5-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanone 
• 1616406-37-1 C₁₅H₁₀Cl₃N₃O 
• 1616405-92-5 2-(2-amino-6-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanol 
• 1616406-38-2 2-(2-amino-5-chloro-1H-benzo[d]imidazol-1-yl)-1-(2,3-dichlorophenyl)ethanol 
• 1221962-60-2 3-amino-N-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)propanoic acid hydrochloride 
• 1221962-62-4 7-Chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]-benz-imidazol-4-one 
• 1221962-61-3 6-chloro-2-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-4-one 

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