121816-79-3

Basic information

• Product Name: 4-bromo-1-methy-2-nitro-1H-imidazole
• Synonyms: 4-bromo-1-methy-2-nitro-1H-imidazole;4-bromo-1-methyl-2-nitroimidazole;4-BROMO-1-METHYL-2-NITRO-1H-IMIDAZOLE
• CAS NO: 121816-79-3
• Molecular Formula: C4H4BrN3O2
• Molecular Weight: 205.99746
• Mol File: 121816-79-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 370.719°C at 760 mmHg
• Flash Point: 178.005°C
• Appearance: /
• Density: 2.043g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-bromo-1-methy-2-nitro-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-1-methy-2-nitro-1H-imidazole(121816-79-3)
• EPA Substance Registry System: 4-bromo-1-methy-2-nitro-1H-imidazole(121816-79-3)

Safety Data

• Hazardous Substances Data: 121816-79-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H4BrN3O2/c1-7-2-3(5)6-4(7)8(9)10/h2H,1H3

Upstream product

• 121816-84-0 4-bromo-2-nitro-1H-imidazole 
• 77-78-1 dimethyl sulfate 
• 1671-82-5 1-methyl-2-nitroimidazole 

Downstream Products

• 1632286-16-8 4-bromo-1-methyl-1H-imidazol-2-amine hydrochloride 

Relevant articles and documents

Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard

A four-step synthesis of 5-[N,N-bis(2-chloroethyl)amino]-1-methyl-2- nitroimidazole from 1-methyl2-nitroimidazole is described. This compound showed similar hypoxia-selective cytotoxicity to the dinitrobenzamide mustard SN 23862 in UV4 cells (ca. 40-fold), and superior selectivity (>7-fold) in repaircompetent AA8 cells.

Synthesis and Reactions of Brominated 2-Nitroimidazoles

Various approaches to the synthesis of the hitherto-unknown 4(5)-bromo-2-nitroimidazole (5) are reported.Direct bromination of 2-nitroimidazole with N-bromosuccinimide gave the unreported 4,5-dibromo-2-nitroimidazole (10) in quantitative yield, but this could be selectively debrominated to give compound (5).While 1-methyl-2-nitroimidazole readily gave 4-bromo-1-methyl-2-nitroimidazole (15) on bromination, this could not be demethylated to give (5), and bromination of various other N-protected 2-nitroimidazoles was also unsuccessful.Lithiation of 4-bromo-1-tritylimidazole (21) followed by quenching with propyl nitrate gave (after detritylation and methylation) a mixture of a dimer (28) and compound (15), indicating that the desired product (5) is produced in this reaction although it can only be isolated in derivatized form.The proposed route for formation of the dimer suggests a general reaction between 1-alkyl-4-bromo-2-nitroimidazoles and strong C- and N-nucleophiles, resulting in substitution at the 5-position.