73902-59-7

Basic information

• Product Name: N¹-benzyl-4-methylbenzimidazole
• CAS NO: 73902-59-7
• Molecular Weight: 222.29
• Mol File: 73902-59-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N¹-benzyl-4-methylbenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: N¹-benzyl-4-methylbenzimidazole(73902-59-7)
• EPA Substance Registry System: N¹-benzyl-4-methylbenzimidazole(73902-59-7)

Safety Data

• Hazardous Substances Data: 73902-59-7(Hazardous Substances Data)

Upstream product

• 4887-83-6 4-methylbenzimidazole 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 4887-83-6 4-methylbenzimidazole 

Relevant articles and documents

Michael adducts in regioselective synthesis of N-substituted azoles

Michael adducts of azoles (4-phenyl-, 4-methyl- and 4-nitroimidazole, 4-methylbenzimidazole, 1,2,4-triazole and theophylline) are shown to be valuable substrates for obtaining the N-substituted derivatives of the parent heterocycles by a quaternization-Hofmann elimination sequence. The effectiveness of the procedure is dependent on the regiochemical outcome of the first, N-protective step, i.e. the Michael addition. By choosing the appropriate Michael acceptor, alkylating agent and deprotection conditions, the thermodynamically less stable regioisomers of N-substituted azoles have been obtained in high yields.

Ambident Heterocyclic Reactivity: Alkylation of 4-Substituted and 2,4-Disubstituted Benzimidazoles

The N1/N3-alkylation patterns of 4-amino-, 4-methyl- and 4-nitro-benzimidazole anions, and their 2-methyl analogues, with a standard set of primary alkyl halides (in dimethylformamide, 30 deg) have been determined and compared.The observed regioselectivities are dominated by proximal effects - electrostatic field, non-bonded steric and in some cases specific association (hydrogen bonding) - the interplay of which is critically dependent on the (variable) geometries of the SN2 transition states involved, in particular on the N---C distance of the developing N-alkyl bonds.The presence of a symmetrically placed 2-methyl group produces an enhanced N1/N3 site selectivity, very sensitive to the loose-tight nature of the transition state.Halide leaving group effects on butylation regioselectivities of 2-unsubstituted, 2-ethoxy-, 2-methyl- and 2-chloro-4-methylbenzimidazole anions, whilst small, are consistent with a Bell-Evans-Polanyi analysis of SN2 transition state variations, with the earlier transition states of CH3(CH2)3I leading to reduced regioselectivities.