26663-77-4

Basic information

• Product Name: METHYL 1H-BENZIMIDAZOLE-5-CARBOXYLATE
• Synonyms: METHYL BENZIMIDAZOLE-5-CARBOXYLATE;METHYL 1H-BENZIMIDAZOLE-5-CARBOXYLATE;AKOS BBS-00000245;1H-Benzimidazole-5-carboxylicacid,methylester(9CI);methyl 1H-benzo[d]imidazole-5-carboxylate;1H-Benzimidazole-5-carboxylic acid methyl ester;Benzimidazole-5-carboxylic acid methyl ester;1H-BenziMidazole-6-carboxylic Acid Methyl Ester
• CAS NO: 26663-77-4
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Product Categories: BENZIMIDAZOLE;pharmacetical;Esters;Imidazoles & Benzimidazoles;Imidazoles & Benzimidazoles;Aromatics;Heterocycles;Intermediates;Miscellaneous Reagents
• Mol File: 26663-77-4.mol
• Article Data: 27

Chemical Properties

• Melting Point: 139 °C
• Boiling Point: 416.181 °C at 760 mmHg
• Flash Point: 205.499 °C
• Appearance: /
• Density: 1.325 g/cm³
• Vapor Pressure: 3.9E-07mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 11.67±0.10(Predicted)
• CAS DataBase Reference: METHYL 1H-BENZIMIDAZOLE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 1H-BENZIMIDAZOLE-5-CARBOXYLATE(26663-77-4)
• EPA Substance Registry System: METHYL 1H-BENZIMIDAZOLE-5-CARBOXYLATE(26663-77-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 26663-77-4(Hazardous Substances Data)

Usage

Description

Methyl 1H-Benzimidazole-5-carboxylate is an organic compound that serves as a key intermediate in the synthesis of various bioisosteric benzimidazoles. These benzimidazoles are known to be potent inhibitors of human cytosolic phospholipase A2α, an enzyme involved in inflammatory processes.

Uses

Used in Pharmaceutical Industry:
Methyl 1H-Benzimidazole-5-carboxylate is used as a chemical intermediate for the synthesis of bioisosteric benzimidazoles. These benzimidazoles are employed as inhibitors of human cytosolic phospholipase A2α, a key enzyme in inflammatory processes. By inhibiting this enzyme, these benzimidazoles can potentially help in the development of anti-inflammatory drugs and other therapeutic agents.

InChI:InChI=1/C9H8N2O2/c1-13-9(12)6-2-3-7-8(4-6)11-5-10-7/h2-5H,1H3,(H,10,11)

Upstream product

• 67-56-1 methanol 
• 15788-16-6 1H-benzimidazole-6-carboxylic acid 
• 36692-49-6 Methyl 3,4-diaminobenzoate 
• 149-73-5 trimethyl orthoformate 
• 122-51-0 orthoformic acid triethyl ester 
• 124-38-9 carbon dioxide 
• 4252-31-7 N-formylbenzamide 
• 119072-55-8 tert-butylisonitrile 
• 15788-16-6 5-benzimidazolecarboxylic acid 
• 106429-29-2 5-(hydroxymethyl)-benzimidazole 
• 64-18-6 formic acid 
• 22907-68-2 3,4-dinitrobenzoic acid methyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 144-62-7 oxalic acid 

Downstream Products

• 222987-27-1 1-Trityl-1H-Benzimidazole-5-carboxylic acid methyl ester 
• 181284-95-7 methyl 5-amino-1H-benzimidazole-6-carboxylate 
• 895581-52-9 methyl 5-amino-1-benzyl-1H-benzimidazole-6-carboxylate 
• 895581-49-4 methyl 6-amino-1-(2-phenylethyl)-1H-benzimidazole-5-carboxylate 
• 895581-48-3 methyl 6-nitro-1-(2-phenylethyl)-1H-benzimidazole-5-carboxylate 
• 895581-43-8 methyl 5-amino-1-benzyl-4-iodo-1H-benzimidazole-6-carboxylate 
• 895581-54-1 methyl 5-amino-1-benzyl-4-(2-phenylethynyl)-1H-benzimidazole-6-carboxylate 
• 895581-55-2 methyl 5-amino-1-benzyl-4-[2-(4-methylphenyl)ethynyl]-1H-benzimidazole-6-carboxylate 
• 895581-56-3 methyl 5-amino-1-benzyl-4-[2-(4-methoxyphenyl)ethynyl]-1H-benzimidazole-6-carboxylate 
• 239482-69-0 (1-trityl-1H-benzimidazol-5-yl)methanol 
• 401947-06-6 C-(1-trityl-1H-benzoimidazol-5-yl)-methylamine 
• 168830-92-0 5-chloromethyl-1-trityl-1H-benzoimidazole 
• 629670-19-5 N-methyl-1H-1,3-benzodiazole-5-carboxamide 
• 181866-90-0 methyl 3-trityl-3H-benzimidazole-5-carboxylate 

Relevant articles and documents

ARYL AND HETEROARYL-CARBOXAMIDE SUBSTITUTED HETEROARYL COMPOUNDS AS TYK2 INHIBITORS

Novel carboxamide substituted compounds of Formula (I) are disclosed; as well as processes for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Tyrosine Kinase 2 (Tyk2).

Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical

A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.

Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones

N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.