60418-14-6

Basic information

• Product Name: 1H-Benzimidazole, 1-methyl-2-(2-nitrophenyl)-
• Synonyms: 1-methyl-2-(2-nitrophenyl)-1H-benzimidazole;1-Methyl-2-(2-nitro-phenyl)-1H-benzimidazol;N-methyl-2-(o-nitrophenyl)benzimidazole;1-methyl-2-(2-nitro-phenyl)-1H-benzoimidazole;1-methyl-2-(2'-nitrophenyl)benzimidazole
• CAS NO: 60418-14-6
• Molecular Formula: C14H11N3O2
• Molecular Weight: 253.26
• Mol File: 60418-14-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1H-Benzimidazole, 1-methyl-2-(2-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole, 1-methyl-2-(2-nitrophenyl)-(60418-14-6)
• EPA Substance Registry System: 1H-Benzimidazole, 1-methyl-2-(2-nitrophenyl)-(60418-14-6)

Safety Data

• Hazardous Substances Data: 60418-14-6(Hazardous Substances Data)

Upstream product

• 2208-58-4 2-(2-nitrophenyl)-1H-benzimidazole 
• 74-88-4 methyl iodide 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 552-89-6 2-nitro-benzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 1632-83-3 1-Methylbenzimidazole 
• 552-16-9 ortho-nitrobenzoic acid 
• 2622-63-1 1-methyl-2-phenylbenzimidazole 
• 88-73-3 2-Chloronitrobenzene 
• 612-28-2 2-nitro-N-methylaniline 
• 3717-98-4 N-methyl-N'-(2-nitro-benzylidene)-o-phenylenediamine 
• 3717-99-5 1-methyl-2-(2-nitrophenyl)-2,3-dihydrobenzimidazole 
• 25148-68-9 N-methylbenzene-1,2-diamine dihydrochloride 

Downstream Products

• 29528-19-6 2-(1-methyl-1H-benzo[d]imidazol-2-yl)aniline 
• 155228-12-9 1-methoxy-2-(1-methyl-1H-benzimidazol-2-yl)benzene 
• 60418-17-9 2-(2-azidophenyl)-1-methylbenzimidazole 

Relevant articles and documents

Copper-Catalyzed Chelation-Assisted ortho-Nitration of 2-Aryls Using Pharmacophoric Benzothiazoles and Benzoxazoles as Directing Groups

A copper-catalyzed chelation-assisted ortho-nitration reaction of aryl derivtives has been achieved, using benzazoles as efficient directing groups. The reaction is general and efficient for aryl derivatives with various electronic properties, and also with different pharmacophorically important directing groups, i.e., benzoxazoles, benzothiazoles, and benzimidazoles. The nitro-group-containing products have significance as fluorogenic compounds and potential nitroreductase substrates that could be used for the detection of clinically important microorganisms. The nitration reaction proceeds with an inexpensive copper catalyst and a mild, cheap, and environmentally friendly nitro source, Fe(NO3)3·9H2O. This operationally simple and functional-group-tolerant protocol for the nitration of 2-aryl benzazoles proceeds with a high regioselectivity without the exclusion of air or moisture.

Palladium-catalyzed ortho-nitration of 2-arylbenzoxazoles

An efficient and general protocol for palladium-catalyzed chelation-assisted ortho-nitration of 2-arylbenzoxazoles has been developed. This nitration exhibits high regioselectivity for the substrates, and the reaction could tolerate many functional groups such as F, Cl, Br, CH3, CH3O, affording ortho-nitration products in moderate to good yields. Moreover, some 2-arylbenzoxazole heterocyclic analogues proceed well under this catalytic system. Further studies have been performed to obtain insight into the mechanism.

A Keggin heteropoly acid as an efficient catalyst for an expeditious, one-pot synthesis of 1-methyl-2-(hetero)arylbenzimidazoles

The Keggin heteropoly acid, silicotungstic acid, H4SiW12O40, has been demonstrated to be highly efficient for an expeditious, one-pot synthesis of 1-methyl-2-(hetero)arylbenzimidazoles from N-methyl-1,2-phenylenediamine and (hetero)aryl aldehydes in ethyl acetate at room temperature. The catalyst works equally well for N-phenyl-1,2-phenylenediamine.