25148-68-9

Basic information

• Product Name: N-Methyl-1,2-benzenediamine dihydrochloride
• Synonyms: 2-METHYLAMINOANILINE HYDROCHLORIDE;N-METHYL-O-PHENLENEDIAMINE DIHYDROCHLORIDE;N-METHYL-O-PHENYLENEDIAMINE DIHYDROCHLORIDE;N-METHYL-O-PHENYLENEDIAMINE HYDROCHLORIDE;N-METHYL-1,2-PHENYLENEDIAMINE DIHYDROCHLORIDE;N-METHYL-1,2-PHENYLENEDIAMINE HYDROCHLORIDE;N-METHYL-1,2-BENZENEDIAMINE DIHYDROCHLORIDE;2-benzenediamine,n-methyl-dihydrochloride
• CAS NO: 25148-68-9
• Molecular Formula: C₇H₁₀N₂*2ClH
• Molecular Weight: 195.09
• EINECS: 246-655-8
• Product Categories: Chemical intermediate for Telmisartan;INTERMEDIATESOF;Aromatics Compounds;Aromatics
• Mol File: 25148-68-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 191°C
• Boiling Point: 252.4 °C at 760 mmHg
• Flash Point: 122.4 °C
• Appearance: redish powder
• Vapor Pressure: 0.0193mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: >=10 g/100 mL at 23 ºC
• CAS DataBase Reference: N-Methyl-1,2-benzenediamine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-1,2-benzenediamine dihydrochloride(25148-68-9)
• EPA Substance Registry System: N-Methyl-1,2-benzenediamine dihydrochloride(25148-68-9)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN 2811 6.1/PG III
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 25148-68-9(Hazardous Substances Data)

Usage

Uses

N-Methyl-o-phenylenediamine, Dihydrochloride (cas# 25148-68-9) is a compound useful in organic synthesis.

General Description

Crystals (from ethanol); light purple powder.

Air & Water Reactions

Water soluble.

Reactivity Profile

N-Methyl-1,2-benzenediamine dihydrochloride is an acidic salt. Materials in this group are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.

Fire Hazard

Flash point data for N-Methyl-1,2-benzenediamine dihydrochloride are not available; however, N-Methyl-1,2-benzenediamine dihydrochloride is probably combustible.

InChI:InChI=1/C7H10N2.2ClH/c1-9-7-5-3-2-4-6(7)8;;/h2-5,9H,8H2,1H3;2*1H

Synthetic route

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + 4-methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid (152628-03-0) → 2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole (152628-02-9)

Conditions	Yield
With methanesulfonic acid In i-Amyl alcohol at 130 - 135℃; for 18h; Temperature; Solvent; Reagent/catalyst;	93%
Stage #1: N-methylbenzene-1,2-diamine dihydrochloride; 4-methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid With PPA at 70 - 135℃; for 13.5h; Stage #2: With ammonia In water at 30 - 90℃; for 1h; pH=8.0 - 8.5;	77.4%
With PPA at 150℃; for 20h;	5.86 g
With polyphosphoric acid at 150℃; for 14h;

glycolic Acid (79-14-1) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → (1-methyl-1H-benzimidazol-2-yl)methanol (7467-35-8)

Conditions	Yield
In water for 1.5h; Reflux;	90%
In water Reflux;

glycolic Acid (79-14-1) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2-chloromethyl-1-methyl-1H-benzimidazole (4760-35-4)

Conditions	Yield
Stage #1: glycolic Acid; N-methylbenzene-1,2-diamine dihydrochloride With hydrogenchloride In water Reflux; Stage #2: With thionyl chloride for 3h;	90%

4-fluorobenzaldehyde (459-57-4) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2-(4-fluorophenyl)-1-methyl-1H-benzo[d]imidazole (724-59-4)

Conditions	Yield
Stage #1: N-methylbenzene-1,2-diamine dihydrochloride With triethylamine In o-xylene; para-xylene; m-xylene at 120℃; for 0.5h; Green chemistry; Stage #2: 4-fluorobenzaldehyde With potassium carbonate; 1-methyl-3-(n-butyl)imidazolium iodide In o-xylene; para-xylene; m-xylene at 120℃; for 10h; Green chemistry;	87%

6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (99199-60-7) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2-(6-fluoro-3,4-dihydro-2H-chroman-2-yl)-1-methyl-1H-benzimidazole

Conditions	Yield
With hydrogenchloride In water for 6h; Heating;	83%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + 2-(benzo[d]isoxazol-3-yl)acetic acid (4865-84-3) → 2-((benzo[d]isoxazol-3-yl)methyl)-1-methyl-1H-benzimidazole (854019-04-8)

Conditions	Yield
With hydrogenchloride for 6h; Heating;	83%

1,1-cyclohexanediacetic acid (4355-11-7) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 1,1‑bis(1‑methyl‑benzoimidazol‑2‑ylmethyl)cyclohexane

Conditions	Yield
Stage #1: 1,1-cyclohexanediacetic acid; N-methylbenzene-1,2-diamine dihydrochloride With phosphoric acid at 180℃; for 6h; Stage #2: With sodium hydroxide In water pH=7 - 8;	83%

2-(2-carboxyphenyl)benzimidazole (16529-06-9) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2-[2-(benzimidazol-2-yl)phenyl]-1-methylbenzimidazole

Conditions	Yield
With phosphoric acid at 180℃; for 4h;	83%

2-acetoxybenzaldehyde (5663-67-2) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 1,2-dimethyl-1H-benzimidazole (2876-08-6) + 1-Acetyl-2-(2-hydroxyphenyl)-3-methylbenzimidazolin (97272-83-8)

Conditions	Yield
In pyridine 1.) 2 h, room temperature, 2.) 16 h, 44 deg C;	A n/a B 80%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + chelidamic acid (138-60-3) → bis(2,6-bis(1'-methylbenzimidazolyl)-4-hydroxypyridine)

Conditions	Yield
With phosphoric acid	78%

2,3-diaminephenazine (655-86-7) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 5,14-dihydro-5,7,12,14-tetraazapentacene (111076-33-6)

Conditions	Yield
With hydrogenchloride; sodium chloride In water at 320℃; for 0.0833333h;	77%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 3-(1-methyl-1H-benzimidazol-2-yl)propan-1-ol (116040-91-6)

Conditions	Yield
In hydrogenchloride	71%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + 2-Hydroxyphenylacetic acid (614-75-5) → 2-(2'-hydroxybenzyl)-N-methylbenzimidazole (123771-27-7)

Conditions	Yield
With hydrogenchloride for 75h; Heating;	70%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + benzene-1,2-dicarboxylic acid (88-99-3) → 1,2-bis(N-methylbenzimidazol-2'-yl)benzene (178814-07-8)

Conditions	Yield
With polyphosporic acid at 200℃; for 4h;	70%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2-chloromethyl-1-methyl-1H-benzimidazole (4760-35-4)

Conditions	Yield
With hydrogenchloride; chloroacetic acid for 8h; Reflux;	70%
With sodium hydroxide; chloroacetic acid In hydrogenchloride

3,3'-Iminodipropionitrile (111-94-4) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → N,N-bis<2-(1'-methyl-2'-benzimidazolyl)ethyl>amine (131296-87-2)

Conditions	Yield
With hydrogenchloride for 100h; Heating;	67%

4-tert-Butylbenzaldehyde (939-97-9) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2-(4-(tert-butyl)phenyl)-1-methyl-1H-benzo[d]imidazole (1437793-93-5)

Conditions	Yield
Stage #1: N-methylbenzene-1,2-diamine dihydrochloride With triethylamine In o-xylene; para-xylene; m-xylene at 120℃; for 0.5h; Green chemistry; Stage #2: 4-tert-Butylbenzaldehyde With potassium carbonate; 1-methyl-3-(n-butyl)imidazolium iodide In o-xylene; para-xylene; m-xylene at 120℃; for 10h; Green chemistry;	64%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + chloroacetic acid (79-11-8) → 2-chloromethyl-1-methyl-1H-benzimidazole (4760-35-4)

Conditions	Yield
With hydrogenchloride for 18h; Heating;	61%
In water Reflux;

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + iminodiacetic acid (142-73-4) → N,N-bis((1-methylbenzimidazol-2-yl)methyl)amine (152037-48-4)

Conditions	Yield
With hydrogenchloride for 24h; Heating;	61%

N-butyryl-4-amino-3-methyl-5-nitrobenzoic acid (959987-48-5) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → N-(2-aminophenyI)-4-(butyramido)-N,3-dimethyl-5-nitrobenzamide (959987-49-6)

Conditions	Yield
Stage #1: N-methylbenzene-1,2-diamine dihydrochloride With pyridine In dichloromethane at 20℃; Stage #2: N-butyryl-4-amino-3-methyl-5-nitrobenzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran; dichloromethane	61%

isophthalic acid (121-91-5) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 1,3-bis(1-methyl-1H-benzimidazol-2-yl)benzene (141045-26-3)

Conditions	Yield
With phosphoric acid at 200℃; for 4h;	60%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + ortho-anisaldehyde (135-02-4) → 1-methoxy-2-(1-methyl-1H-benzimidazol-2-yl)benzene (155228-12-9)

Conditions	Yield
Stage #1: N-methylbenzene-1,2-diamine dihydrochloride With triethylamine In o-xylene; para-xylene; m-xylene at 120℃; for 0.5h; Green chemistry; Stage #2: ortho-anisaldehyde With potassium carbonate; 1-methyl-3-(n-butyl)imidazolium iodide In o-xylene; para-xylene; m-xylene at 120℃; for 10h; Green chemistry;	60%

3,3'-<(propane-1,3-diyl)bis(thio)>bis (5065-18-9) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 1,7-bis(N-methyl-1H-benzimidazol-2-yl)-2,6-dithiaheptane (92462-67-4)

Conditions	Yield
In hydrogenchloride for 17h; Ambient temperature;	50%

4-(2-carboxyethyl)-4-nitroheptanedioic acid (59085-15-3) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → Tris<2-(1-methylbenzimidazol-2-yl)ethyl>nitromethane

Conditions	Yield
With hydrogenchloride for 20h; Heating;	50%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + 2-methylphenyl aldehyde (529-20-4) → 1-methyl-2-(o-tolyl)-1H-benzo[d]imidazole (31815-61-9)

Conditions	Yield
Stage #1: N-methylbenzene-1,2-diamine dihydrochloride With triethylamine In o-xylene; para-xylene; m-xylene at 120℃; for 0.5h; Green chemistry; Stage #2: 2-methylphenyl aldehyde With potassium carbonate; 1-methyl-3-(n-butyl)imidazolium iodide In o-xylene; para-xylene; m-xylene at 120℃; for 10h; Green chemistry;	50%

N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) + 4-bromo-benzaldehyde (1122-91-4) → 2-(4-bromophenyl)-1-methyl-1H-benzo[d]imidazole (2751-84-0)

Conditions	Yield
Stage #1: N-methylbenzene-1,2-diamine dihydrochloride With triethylamine In o-xylene; para-xylene; m-xylene at 120℃; for 0.5h; Green chemistry; Stage #2: 4-bromo-benzaldehyde With potassium carbonate; 1-methyl-3-(n-butyl)imidazolium iodide In o-xylene; para-xylene; m-xylene at 120℃; for 10h; Green chemistry;	49%

2-bromo-3,4,5-tri-methoxybenzaldehyde (35274-53-4) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2-(2-bromo-3,4,5-trimethoxyphenyl)-1-methyl-1H-benzoimidazole (1444017-99-5)

Conditions	Yield
With dihydrogen peroxide In acetonitrile at 20℃; for 24h; Inert atmosphere;	48%

1H-1,2,3-triazole-4,5-dicarboxylic acid (4546-95-6) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 1-methyl-2-(3H-[1,2,3]triazol-4-yl)-1H-benzoimidazole (1389396-26-2)

Conditions	Yield
With hydrogenchloride In water at 120℃;	43%

1H-1,2,3-triazole-4,5-dicarboxylic acid (4546-95-6) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 5-(1-methyl-1H-benzo[d]imidazol-2-yl)-3H-1,2,3-triazole-4-carboxylic acid (1389396-26-2)

Conditions	Yield
With hydrogenchloride In water at 120℃;	42.7%

Pyridine-2,6-dicarboxylic acid (499-83-2) + N-methylbenzene-1,2-diamine dihydrochloride (25148-68-9) → 2,6-bis(1-methyl-1H-benzo[d]imidazol-2-yl)pyridine (112362-30-8)

Conditions	Yield
With PPA at 170℃; for 3h;	15%

Downstream Products

• 14754-42-8 2-ethyl-1-methyl-1H-benzo[d]imidazole 
• 65463-69-6 2-(4-chloro-3-methyl-phenoxy)-1-methyl-2,3-dihydro-1H-benzo[1,3,2]diazaphosphole 2-oxide 
• 112362-30-8 2,6-bis(1-methyl-1H-benzo[d]imidazol-2-yl)pyridine 
• 141045-26-3 1,3-bis(1-methyl-1H-benzimidazol-2-yl)benzene 
• 144701-48-4 telmisatran 
• 141838-54-2 4'-(1-Methyl-2'-propyl-1H-[2,5']bibenzoimidazolyl-3'-ylmethyl)-biphenyl-2-carboxylic acid tert-butyl ester 
• 144702-26-1 tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate 
• 97272-84-9 1-Acetyl-2-(2-methoxyphenyl)-3-methylbenzimidazolin 
• 13038-85-2 1-methyl-2-guanidinobenzimidazole 
• 60418-14-6 1-methyl-2-(2-nitrophenyl)-1H-benzo[d]imidazole 
• 3718-03-4 1-methyl-2-(4-nitrophenyl)-1H-benzimidazole 
• 1632-83-3 1-Methylbenzimidazole 
• 31815-61-9 1-methyl-2-(o-tolyl)-1H-benzo[d]imidazole 
• 155228-12-9 1-methoxy-2-(1-methyl-1H-benzimidazol-2-yl)benzene