53484-16-5

Basic information

• Product Name: 6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE
• Synonyms: 6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE;6-Bromo-1-methyl-1H-benzimidazole;1-Methyl-6-bromobenzimidazole;6-bromo-1-methyl-1H-1,3-benzodiazole
• CAS NO: 53484-16-5
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.05858
• Product Categories: blocks;Bromides;Imidazoles
• Mol File: 53484-16-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 317.2 °C at 760 mmHg
• Flash Point: 145.7 °C
• Appearance: /
• Density: 1.60
• Vapor Pressure: 0.00039mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.47±0.10(Predicted)
• CAS DataBase Reference: 6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE(53484-16-5)
• EPA Substance Registry System: 6-BROMO-1-METHYL-1H-BENZO[D]IMIDAZOLE(53484-16-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 53484-16-5(Hazardous Substances Data)

Usage

General Description

6-Bromo-1-methyl-1H-benzo[d]imidazole is a chemical compound with the molecular formula C8H7BrN2. It is a brominated derivative of benzimidazole, which is a heterocyclic compound containing a fused benzene and imidazole ring system. 6-Bromo-1-methyl-1H-benzo[d]imidazole is widely used in organic synthesis as a building block for the preparation of various pharmaceuticals, agrochemicals, and materials. It is also used as a reagent in the synthesis of biologically active compounds, such as kinase inhibitors and antiviral agents. Due to its versatile reactivity and wide range of applications, 6-Bromo-1-methyl-1H-benzo[d]imidazole is an important intermediate in the chemical industry.

InChI:InChI=1/C8H7BrN2/c1-11-5-10-7-3-2-6(9)4-8(7)11/h2-5H,1H3

Upstream product

• 337915-79-4 4-bromo-N²-methylbenzene-1,2-diamine 
• 149-73-5 trimethyl orthoformate 
• 302800-13-1 5-bromo-N-methyl-2-nitroaniline 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 64-18-6 formic acid 
• 4887-88-1 5-bromo-1H-benzo[d]imidazole 
• 74-88-4 methyl iodide 
• 122-51-0 orthoformic acid triethyl ester 
• 67-56-1 methanol 

Downstream Products

• 10406-94-7 1-methyl-6-chloro-1H-benzo[d]imidazole 
• 1616099-43-4 3-(1-methyl-1H-benzo[d]imidazol-6-yl)aniline 
• 1616059-85-8 C₁₇H₁₆N₂O₂ 
• 1616059-76-7 3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenol 
• 1616059-77-8 1-methyl-6-(3-(oxiran-2-ylmethoxy)phenyl)-1H-benzo[d]imidazole 
• 26530-93-8 1-methyl-6-amino-1H-benzo[d]imidazole 
• 50591-23-6 1-methyl-1H-benzo[d]imidazol-6-ol 
• 181867-19-6 1-methyl-1H-benzo[d]imidazole-6-carbaldehyde 

Relevant articles and documents

Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of N-Heterocycles via Manganese-Catalyzed Dehydrogenative Cyclization

The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese-catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile synthesis of N-heterocycles. The in situ generated formaldehyde via catalytic methanol dehydrogenation can be selectively trapped by diverse dinucleophiles to avoid several possible side reactions. The utility of this transformation is further highlighted by its successful application to the synthesis of 13C-labeled N-heterocycles using 13CH3OH as a readily accessible 13C-isotope reagent.

Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

Alkylation of 4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (1b) with iodomethane in THF using NaHMDS as base selectively provided N2-methyl product 4-methoxy-2-methyl-2H-pyrazolo[3,4-d]pyrimidine (3b) in an 8/1 ratio over N1-methyl product (2b). Interestingly, conducting the reaction in DMSO reversed selectivity to provide a 4/1 ratio of N1/N2 methylated products. Crystal structures of product 3b with N1 and N7 coordinated to sodium indicated a potential role for the latter reinforcing the N2-selectivity. Limits of selectivity were tested with 26 heterocycles which revealed that N7 was a controlling element directing alkylations to favor N2 for pyrazolo- and N3 for imidazo- and triazolo-fused ring heterocycles when conducted in THF. Use of 1H-detected pulsed field gradient-stimulated echo (PFG-STE) NMR defined the molecular weights of ionic reactive complexes. This data and DFT charge distribution calculations suggest close ion pairs (CIPs) or tight ion pairs (TIPs) control alkylation selectivity in THF and solvent-separated ion pairs (SIPs) are the reactive species in DMSO.

BENZIMIDAZOLE DERIVATIVES AND USES THEREOF

Benzimidazole derivatives of Formula I, that modulate the activity of ACSS2 are disclosed for therapeutic use. The fused imidazole ring of the compounds disclosed has a diarylmethyl or diarylmethanol moiety attached at the 2-position and the compounds have at least one other substituent at the 5 or 6 position of the benzimidazole. Also disclosed are methods of using the benzimidazole compounds for the treatment of diseases or disorders, such as cancer.