53484-15-4

Basic information

• Product Name: 5-Bromo-1-methyl-1H-benzo[d]imidazole
• Synonyms: 5-Bromo-1-methyl-1H-benzo[d]imidazole;5-BROMO-1-METHYL-1H-BENZIMIDAZOLE;5-Bromo-1-methylbenzimidazole;5-bromo-1-methyl-1H-1,3-benzodiazole
• CAS NO: 53484-15-4
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.07
• Product Categories: blocks;Bromides;Imidazoles
• Mol File: 53484-15-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 317.2±34.0 °C(Predicted)
• Flash Point: 145.7 °C
• Appearance: /
• Density: 1.60
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.56±0.10(Predicted)
• CAS DataBase Reference: 5-Bromo-1-methyl-1H-benzo[d]imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1-methyl-1H-benzo[d]imidazole(53484-15-4)
• EPA Substance Registry System: 5-Bromo-1-methyl-1H-benzo[d]imidazole(53484-15-4)

Safety Data

• Hazardous Substances Data: 53484-15-4(Hazardous Substances Data)

Usage

General Description

5-Bromo-1-methyl-1H-benzo[d]imidazole is a chemical compound that belongs to the class of benzo[d]imidazoles. It is a derivative of benzoimidazole with a bromine atom at the 5th position and a methyl group at the 1st position of the imidazole ring. 5-Bromo-1-methyl-1H-benzo[d]imidazole has potential applications in the pharmaceutical industry as a building block for the synthesis of new pharmaceuticals and drug candidates. It is also used in chemical research and in the development of new materials. 5-Bromo-1-methyl-1H-benzo[d]imidazole is available as a white to beige solid and should be handled and stored with proper safety measures due to its potential hazards.

Upstream product

• 64-18-6 formic acid 
• 69038-76-2 2-N-methylamino-5-bromoaniline 
• 149-73-5 trimethyl orthoformate 
• 364-73-8 4-Bromo-1-fluoro-2-nitrobenzene 
• 53484-26-7 N-methyl-4-bromo-2-nitroaniline 
• 4887-88-1 5-bromo-1H-benzo[d]imidazole 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 124-38-9 carbon dioxide 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 1453854-08-4 (2R,3S,4R,5S,6R)-2-(hydroxymethyl)-6-(3-(1-methyl-1H-benzo[d]imidazol-5-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triol 
• 10394-38-4 1-methyl-1H-benzo[d]imidazol-5-amine 
• 34594-86-0 N,1-dimethyl-1H-benzo[d]imidazol-5-amine 
• 1107627-02-0 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole 
• 628710-60-1 4-methoxy-3-(1'-methylbenzimidazol-5'-yl)benzenecarboxaldehyde 

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.

INHIBITORS OF FIBROBLAST GROWTH FACTOR RECEPTOR KINASES

Provided herein are heteroaryl inhibitors of fibroblast growth factor receptor kinases, pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of diseases.

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.