86072-07-3

Basic information

• Product Name: 2-chloro-1-methyl-5-nitro-imidazole
• Synonyms: 2-chloro-1-methyl-5-nitro-imidazole;2-CHLORO, 3-METHYL, 4-NITROIMIDAZOL
• CAS NO: 86072-07-3
• Molecular Formula: C₄H₄ClN₃O₂
• Molecular Weight: 161.55
• Mol File: 86072-07-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 333.9°C at 760 mmHg
• Flash Point: 155.7°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 0.000132mmHg at 25°C
• Refractive Index: 1.648
• CAS DataBase Reference: 2-chloro-1-methyl-5-nitro-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-1-methyl-5-nitro-imidazole(86072-07-3)
• EPA Substance Registry System: 2-chloro-1-methyl-5-nitro-imidazole(86072-07-3)

Safety Data

• Hazardous Substances Data: 86072-07-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H4ClN3O2/c1-7-3(8(9)10)2-6-4(7)5/h2H,1H3

Upstream product

• 57531-37-0 2-chloro-4-nitro-1H-imidazole 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 

Downstream Products

• 56302-13-7 1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one 

Relevant articles and documents

Nitroimidazoles: Part XX- Reactions of 2,4-Dinitroimidazoles with 2-Haloethanols, 3-Chloropropionitrile and Propylene Oxide

The reaction of 2,4-dinitroimidazole (1) with 2-chloroethanol, 3-chloroethanol, 3-chloropropanol or 3-chloropropionitrile gives 2-chloro-4-nitroimidazole (7) and not 4-chloro-5-nitroimidazole (3) as claimed in earlier literature. 1 and 2-bromoethanol likewise yield 2-bromo-4-nitroimidazole (11). 7 is methylated to isomeric methyl derivatives 8 and 13 and 11 to 12 and 14.In the reaction of 1 with 3-chloropropionitrile, other products 9, 10 and 16 have been isolated. 1 is unaffected by 2-chloropentane. 2-Chloroethanol and 1-methyl-2,4-dinitroimidazole (2) afford 8.HCl formed from hot 2-chloroethanol in the presence of nitroimdazoles seems to be responsible for the displacement of NO2 group at position-2 with chlorine. 1 and propylene oxide yield imidazooxazoline (18) and the dinitro alcohol (19) along with a small amount of the isomer 20. 19 is transformed to imidazooxazoline (21) by excess propylene oxide or piperidine. 7 and propylene oxide afford isomeric alcohols 26 and 27, the latter being readily transformed to 18.Piperidine opens the oxazoline ring 18 to yield 25. 1H NMR and 13C NMR data are used to derive new structures.

NITROIMIDAZOLES. PART V. CHLORONITROIMIDAZOLES FROM DINITROIMIDAZOLES. A REINVESTIGATION

5(4)-Chloro-4(5)-nitroimidazole and 2-chloro-4(5)-nitroimidazole or their N-methyl derivatives have been synthesized in at least two independent routes.In contrast to some former reports it has been established that from 2,4(or 5)-dinitroimidazoles only 2-chloro-4(or 5)-nitroimidazoles are obtained.In 4,5-dinitroimidazoles only a nitro group in the 5-position is replaced by a chlorine atom.Structures of the obtained compounds have been confirmed by analyses of physico-chemical data.