58842-61-8

Basic information

• Product Name: 1H-Benzimidazole-5-carboxylicacid,ethylester(9CI)
• Synonyms: 1H-Benzimidazole-5-carboxylicacid,ethylester(9CI);1-(1H-benzo[d]imidazol-5-yl)-2-ethoxyethanone;Ethyl benziMidazole-5-carboxylate;1H-BenziMidazole-6-carboxylic acidethyl ester;Ethyl 1H-benzimidazole-5-carboxylate
• CAS NO: 58842-61-8
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.2
• Product Categories: BENZIMIDAZOLE;pharmacetical
• Mol File: 58842-61-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 417.554 °C at 760 mmHg
• Flash Point: 206.33 °C
• Appearance: /
• Density: 1.272±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 1H-Benzimidazole-5-carboxylicacid,ethylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-5-carboxylicacid,ethylester(9CI)(58842-61-8)
• EPA Substance Registry System: 1H-Benzimidazole-5-carboxylicacid,ethylester(9CI)(58842-61-8)

Safety Data

• Hazardous Substances Data: 58842-61-8(Hazardous Substances Data)

Usage

General Description

1H-Benzimidazole-5-carboxylic acid, ethyl ester (9CI) is a chemical compound with the molecular formula C10H9N3O2. It is a derivative of benzimidazole and is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs and biologically active compounds. It is a pale yellow solid with a melting point of 210-213°C and is slightly soluble in water. 1H-Benzimidazole-5-carboxylicacid,ethylester(9CI) is known for its potential as an antimicrobial, antiviral, and antitumor agent, making it a valuable intermediate in the development of new pharmaceutical products. It is important to handle this compound with care and adhere to proper safety protocols due to its potential health hazards.

InChI:InChI=1/C10H10N2O2/c1-2-14-10(13)7-3-4-8-9(5-7)12-6-11-8/h3-6H,2H2,1H3,(H,11,12)

Upstream product

• 124-38-9 carbon dioxide 
• 37466-90-3 ethyl 3,4-diaminobenzoate 
• 64-18-6 formic acid 
• 619-05-6 3,4-diaminobenzoic acid 
• 64-17-5 ethanol 
• 15788-16-6 1H-benzimidazole-6-carboxylic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 614-97-1 5-methylbenzimidazole 
• 15788-16-6 5-benzimidazolecarboxylic acid 

Downstream Products

• 108038-52-4 1H-benzimidazole-5-carbohydrazide 
• 106429-29-2 (1H-benzo[d]imidazol-6-yl)methanol 
• 106429-29-2 5-(hydroxymethyl)-benzimidazole 
• 108038-52-4 3H-benzo[d]imidazole-5-carbohydrazide 
• 1206789-73-2 N'-[(2-hydroxy-3,5-di-tert-butyl)phenylmethylene]-1H-benzo[d]imidazole-6-formhydrazide 
• 1333405-84-7 5-(5-phenethyl-1,3,4-oxadiazol-2-yl)benzimidazole 
• 1030838-99-3 5-(5-(3-phenylpropylthio)-1,3,4-oxadiazol-2-yl)benzimidazole 
• 1030838-98-2 5-(5-(phenethylthio)-1,3,4-oxadiazol-2-yl)benzimidazole 
• 606091-78-5 C₉H₆N₄OS 
• 1030839-18-9 5-(1H-benzo[d]imidazol-5-yl)-N-(benzyl)-1,3,4-oxadiazol-2-amine 
• 606117-06-0 5-(5-(benzylthio)-1,3,4-oxadiazol-2-yl)benzimidazole 
• 1333406-27-1 5-(5-((3,4-dimethoxyphenylsulfonyl)methyl)-1,3,4-thiadiazol-2-yl)benzimidazole 
• 1333406-26-0 5-(5-((3,4-dimethoxyphenylthio)methyl)-1,3,4-thiadiazol-2-yl)benzimidazole 
• 1333406-25-9 5-(5-((phenylsulfonyl)methyl)-1,3,4-thiadiazol-2-yl)benzimidazole 

Relevant articles and documents

Gold(I) and Gold(III) N-Heterocyclic Carbene Complexes as Antibacterial Agents and Inhibitors of Bacterial Thioredoxin Reductase

A series of (NHC)Au(I)Cl monocarbene complexes and their gold(III) analogues (NHC)Au(III)Cl3 were prepared and investigated as antibacterial agents and inhibitors of bacterial TrxR. The complexes showed stronger antibacterial effects against the Gram-positive MRSA and E. faecium strains than against several Gram-negative bacteria. All complexes were efficient inhibitors of bacterial thioredoxin reductase, indicating that inhibition of this enzyme might be involved in their mechanism of action. The efficacy of gold(I) and gold(III) analogues was comparable in most of the assays. The cytotoxicity of the gold NHC compounds against cancer and human cells was overall weaker than the activity against the Gram-positive bacteria, suggesting that their optimization as antibacterials warrants further investigation.

Cobalt-catalyzed synthesis of N-containing heterocycles: Via cyclization of ortho -substituted anilines with CO2/H2

The CO2-involved synthesis of chemicals is of great significance from the green and sustainable chemistry viewpoint. Herein, we report a non-noble metal catalytic system composed of CoF2, CsF and P(CH2CH2PPh2)3 (denoted as PP3) for the synthesis of N-containing heterocycles from ortho-substituted anilines and CO2/H2. Mechanism investigation indicates that [Co(PP3)H(CO2)]+ is a catalytically active intermediate under working conditions; and CsF plays important roles in activating ortho-substituted anilines via hydrogen bond interactions, thus promoting the formation of the final products. This catalytic system is highly efficient, and allows a wide scope of ortho-substituted anilines, together with excellent functional group tolerance, affording various N-containing heterocycles in good to excellent yields.

C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C-H Activation

Herein, we report a Rh(I)/bisphosphine/K3PO4 catalytic system allowing for the first time the selective branched C-H alkylation of benzimidazoles with Michael acceptors. Branched alkylation with N,N-dimethyl acrylamide was successfully applied to the alkylation of a broad range of benzimidazoles incorporating a variety of N-substituents and with both electron-rich and -poor functionality displayed at different sites of the arene. Moreover, the introduction of a quaternary carbon was achieved by alkylation with ethyl methacrylate. The method was also shown to be applicable to the C2-selective branched alkylation of azabenzimidazoles.