65902-59-2

Basic information

• Product Name: 2-Bromo-4-nitroimidazole
• Synonyms: 2-BROMO-4-NITROIMIDAZOLE;2-Bromo-4-nitro-1H-imidazole;2-Bromo-4-nitroimidazole=2-Bromo-5-nitroimidazole;2-Bromo-4-nitro-1h-imidazole ,98%;2-Bromo-4-nitro-3H-imidazole;2-Bromo-5-nitroimidazole;1H-IMidazole, 2-broMo-5-nitro-;2-BroMo-4-nitroiMidazole98%
• CAS NO: 65902-59-2
• Molecular Formula: C₃H₂BrN₃O₂
• Molecular Weight: 191.97
• EINECS: 1308068-626-2
• Product Categories: Halides;Imidazoles & Benzimidazoles;Imidaxoles;Imidazoles & Benzimidazoles;OLED materials,pharm chemical,electronic
• Mol File: 65902-59-2.mol

Chemical Properties

• Melting Point: 232.0 to 236.0 °C
• Boiling Point: 402.506 °C at 760 mmHg
• Flash Point: 197.229 °C
• Appearance: /Solid
• Density: 2.157 g/cm³
• Vapor Pressure: 1.09E-06mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 5.65±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-4-nitroimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-nitroimidazole(65902-59-2)
• EPA Substance Registry System: 2-Bromo-4-nitroimidazole(65902-59-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 65902-59-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

InChI:InChI=1/C3H2BrN3O2/c4-3-5-1-2(6-3)7(8)9/h1H,(H,5,6)

Upstream product

• 5213-49-0 2,4-dinitro-1H-imidazole 
• 6154-30-9 2,4⁽⁵⁾-dibromo-5⁽⁴⁾-nitroimidazole 
• 683276-47-3 2-bromo-1-methoxymethyl-4-nitroimidazole 
• 6154-30-9 2,4⁽⁵⁾-dibromo-5⁽⁴⁾-nitroimidazole 

Downstream Products

• 16681-63-3 2-bromo-1-methyl-4-nitroimidazole 
• 17024-47-4 2-Bromo-1-methyl-5-nitroimidazole 
• 57531-37-0 2-chloro-4-nitro-1H-imidazole 
• 1188330-38-2 (S)-N-(3-{4-[4-(2-bromo-4-nitro-imidazol-1-ylmethyl)4-hydroxy-piperidin-1-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide 
• 1188337-59-8 3-(2-bromo-4-nitro-imidazol-1-yl)-2-{4-[(R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-propionic acid ethyl ester 
• 1188337-63-4 2-{4-[(S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}3-(2-bromo-4-nitro-imidazol-1-yl)-propionic acid ethyl ester 
• 1263187-96-7 1-(2-bromo-4-nitro-1H-imidazol-1-yl)-3-[4-(trifluoromethoxy)phenoxy]propan-2-ol 
• 1263417-25-9 2-bromo-4-nitro-1-{(2S)-2-{[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]oxy}-3-[triisopropylsilyloxy]propyl}-1H-imidazole 
• 1283135-20-5 2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(2,4-dichlorophenyl)ethanol 
• 1283135-24-9 2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(4-chlorophenyl)ethanol 
• 1283135-22-7 2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(2,4-difluorophenyl)ethanol 
• 1283135-26-1 1-(biphenyl-4-yl)-2-(2-bromo-4-nitro-1H-imidazol-1-yl)ethanol 
• 1283135-23-8 2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(4-fluorophenyl)ethanol 
• 1283135-25-0 2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(4-nitrophenyl)ethanol 

Relevant articles and documents

A concise and sequential synthesis of the nitroimidazooxazole based drug, Delamanid and related compounds

A concise, protection-group free and sequential route has been developed for the synthesis of the nitroimidazole based FDA-approved multi-drug resistant anti-tuberculosis drug, Delamanid and anti-leishmanial lead candidate VL-2098. The synthesis required

Bicyclic nitroimidazole derivatives, preparation method thereof and pharmaceutical composition for prevention or treatment of tuberculosis containing the same as an active ingredient

The present invention relates to a bicyclic nitroimidazole derivative or a pharmaceutically acceptable salt thereof, a method for manufacturing the same, and a pharmaceutical composition comprising the same for preventing or treating tuberculosis. The novel bicyclic nitroimidazole derivative according to the present invention shows a superior antitubercular efficacy for tubercular bacillus in various environments, thereby can be used as a pharmaceutical composition for preventing or treating the tuberculosis.

An improved kilogram-scale synthesis of 2-bromo-4-nitro-1H-imidazole: A key building block of nitroimidazole drugs

An efficient two-step method for the synthesis of 2-bromo-4-nitroimidazole, 6, a key building block for nitroimidazole drugs, has been developed. The synthesis involves dibromination of 4-nitroimidazole 10 followed by selective debromination using in situ reductive deiodination strategy. The reactions are facile, safe, and easy to scale up. The large-scale applicability of this improved method was tested by conducting the reactions on kilogram scale to produce the desired product in high yield and quality.

METHOD FOR PRODUCING 2-HALOIMIDAZOLE COMPOUND

An object is to provide a process for producing a 2-haloimidazole compound represented by the formula (II), which uses inexpensive raw materials and can produce it by simple and convenient operations at low costs. A 2,4-dihaloimidazole compound represente

METHODS FOR THE PRODUCTION OF 2-HALO-4-NITROIMIDAZOLE AND INTERMEDIATES THEREOF

The present invention relates to a method for the production of 2-halo-4-nitroimidazole and intermediates thereof. Further, the present invention relates to a production process of 1,4-dinitroimidazole comprising subjecting 4-nitroimidazole to nitration reaction. Furthermore, the present invention relates to a production process of 4-nitroimidazole comprising subjecting imidazole to nitration reaction.

Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl] oxy}- 6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)

The nitroimidazooxazine S-1 (PA-824) is a new class of bioreductive drug for tuberculosis. A series of related bicyclic nitroheterocycles was synthesized, designed to have a wide range of one-electron reduction potentials E(1) (from -570 to -338 mV, compared with -534 mV for S-1). The observed E(1) values closely correlated with the om values of the heteroatom at the 4/8-position of the adjacent six-membered ring. Although the compounds spanned a range of E(1) values around that of S-1, only the nitroimidazothiazines showed significant antitubercular activity (at a similar level of potency), suggesting that E(1) is not the main driver of efficacy. Furthermore, there was a correlation between activity and the formation of imidazole ring-reduced products at the two-electron level, pointing to the potential importance of this reduction pathway, which is determined by the nature of the substituent at the 2-position of the 4-nitroimidazole ring.

1-SUBSTITUTED 4-NITROIMIDAZOLE COMPOUND AND PROCESS FOR PRODUCING THE SAME

The present invention relates to a 1-substituted-4-nitroimidazole compound represented by the general formula (1) or a salt thereof, (wherein R is a hydrogen atom, a lower alkoxy group-substituted lower alkyl group, a phenyl-lower alkoxy group-substituted lower alkyl group, a cyano-substituted lower alkyl group, a phenyl-lower alkyl group which may have lower alkoxy groups as the substituents in the phenyl ring or a group of the formula -CH2RA; X is a halogen atom or a group of the formula -S(O)n-R1) and method for preparing the same. The compound of the formula (1) is a useful compound as an intermediate for synthesis of various pharmaceutical and agricultural chemicals, particularly, as intermediates for antitubercular agents.

METHOD FOR PRODUCING 4-NITROIMIDAZOLE COMPOUND

The present invention provides a method for producing a 4-nitroimidazole compound represented by general formula (1) at high yield and at high purity by a safe method causing few dangers such as explosion. The production method of the present invention comprises iodinating a 4-nitroimidazole compound represented by general formula (2): wherein each of X1 and X2 represents a chlorine atom or bromine atom, and then reducing the obtained 5-iodo-4-nitroimidazole compound represented by general formula (3): wherein X2 is the same as defined above.

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.