26530-93-8

Basic information

• Product Name: 1H-Benzimidazol-6-amine,1-methyl-(9CI)
• Synonyms: 1H-Benzimidazol-6-amine,1-methyl-(9CI);1H-benzimidazol-6-amine, 1-methyl-;1-methyl-1H-benzimidazol-6-amine;1-methyl-1H-benzimidazol-6-amine(SALTDATA: FREE);1-Methyl-1H-benzo[d]imidazol-6-amine;(3-methylbenzimidazol-5-yl)amine;3-methyl-5-benzimidazolamine;3-methylbenzimidazol-5-amine
• CAS NO: 26530-93-8
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.17716
• Product Categories: BENZIMIDAZOLE
• Mol File: 26530-93-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 160 °C
• Boiling Point: 348.6°C at 760 mmHg
• Flash Point: 164.6°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 4.97E-05mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 6.16±0.10(Predicted)
• CAS DataBase Reference: 1H-Benzimidazol-6-amine,1-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazol-6-amine,1-methyl-(9CI)(26530-93-8)
• EPA Substance Registry System: 1H-Benzimidazol-6-amine,1-methyl-(9CI)(26530-93-8)

Safety Data

• Statements: 41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 26530-93-8(Hazardous Substances Data)

Usage

General Description

1H-Benzimidazol-6-amine,1-methyl-(9CI) is a chemical compound with the molecular formula C8H9N3. It is a derivative of benzimidazole, which is a bicyclic aromatic organic compound. This chemical has a methyl group attached to the nitrogen atom at position 1, and an amine group at position 6 of the benzimidazole ring. It is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Additionally, it has been investigated for its potential biological activities, such as anticancer and antiviral properties. Overall, 1H-Benzimidazol-6-amine,1-methyl-(9CI) is an important and versatile chemical with various applications in the fields of medicine and agriculture.

InChI:InChI=1/C8H9N3/c1-11-5-10-7-3-2-6(9)4-8(7)11/h2-5H,9H2,1H3

Upstream product

• 5381-79-3 1-methyl-6-nitro-1H-benzoimidazole 
• 103248-15-3 1-(N,N-dimethylaminomethyl)-6-nitrobenzimidazole 
• 94-52-0 5-nitrobenzimidazole 
• 94-52-0 6-nitro-1H-benzo[d]imidazole 
• 5381-78-2 1-methyl-5-nitro-1H-benzo[d]imidazole 
• 53484-16-5 6-bromo-1-methyl-1H-benzo[d]imidazole 
• 51-17-2 benzoimidazole 
• 74-88-4 methyl iodide 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 95576-84-4 N₂-methyl-4-nitrobenzene-1,2-diamine 

Downstream Products

• 135939-43-4 1-methyl-6-(p-tolylamino)benzimidazole 
• 245545-79-3 3-{(Z)-1-[(1-methyl-benzimidazol-6-yl)amino]-1-phenylmethylidene}-2-indolinone 
• 744261-45-8 6-(4-fluorophenyl)-2-methyl-N-(1-methyl-1H-benzimidazol-6-yl)nicotinamide 

Relevant articles and documents

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Fusion of 2-(furan-2-yl)thiazole to 1-methyl-1H-benzimidazole

Methylation of 5(6)-nitro-1H-benzimidazole with methyl iodide in the presence of potassium hydroxide and N-methylpyrrolidin-2-one gave a mixture of isomeric 1-methyl-5-nitro- and 1-methyl-6-nitro-1H-benzimidazoles which were reduced with tin in concentrated aqueous HCl on heating. The resulting amines reacted with furan-2-carbonyl chloride in N-methylpyrrolidin-2-one to give furan-2-carboxamides which were treated with excess P2S5 in pyridine. Oxidation of isomeric furan-2-carbothioamides with K3[Fe(CN)6] in alkaline medium afforded a mixture of intramolecular cyclization products, 2-(furan-2-yl)-6-methyl-6H-imidazo[4,5-g][1,3]benzothiazole and 2-(furan-2-yl)-8-methyl-8H-imidazo[4,5-g][1,3]benzothiazole which were separated by column chromatography and identified.

Structure-activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template

In an effort to design inhibitors of human glutaminyl cyclase (QC), we have synthesized a library of N-aryl N-(5-methyl-1H-imidazol-1-yl)propyl thioureas and investigated the contribution of the aryl region of these compounds to their structure-activity relationships as cyclase inhibitors. Our design was guided by the proposed binding mode of the preferred substrate for the cyclase. In this series, compound 52 was identified as the most potent QC inhibitor with an IC50 value of 58 nM, which was two-fold more potent than the previously reported lead 2. Compound 52 is a most promising candidate for future evaluation to monitor its ability to reduce the formation of pGlu-Aβ and Aβ plaques in cells and transgenic animals.