57531-37-0

Basic information

• Product Name: 2-Chloro-4-nitroimidazole
• Synonyms: TIMTEC-BB SBB000100;1H-IMIDAZOLE, 2-CHLORO-4-NITRO-;2-CHLORO-5-NITRO-1H-IMIDAZOLE;2-CHLORO-4-NITROIMIDAZOLE;2-Chloro-4-nitro-1H-imidazole;1H-Imidazole,2-chloro-4-nitro-(9CI);2-CHLORO-4-NITRO-1H-IMIDAZOLE, 98+%;2-Chloro-5-nitroimidazole
• CAS NO: 57531-37-0
• Molecular Formula: C₃H₂ClN₃O₂
• Molecular Weight: 147.52
• EINECS: 1533716-785-6
• Product Categories: NITRO;Halides;Imidazoles & Benzimidazoles;API intermediates;Imidazoles & Benzimidazoles;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 57531-37-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 216-217 °C
• Boiling Point: 386.8 °C at 760 mmHg
• Flash Point: 187.7 °C
• Appearance: /Solid
• Density: 1.74 g/cm³
• Vapor Pressure: 3.45E-06mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)
• PKA: 5.65±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-4-nitroimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-nitroimidazole(57531-37-0)
• EPA Substance Registry System: 2-Chloro-4-nitroimidazole(57531-37-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 57531-37-0(Hazardous Substances Data)

Usage

Description

2-Chloro-4-nitroimidazole is a 4-nitroimidazole derivative characterized by its light yellow solid appearance. It is a compound with potential applications in the medical and pharmaceutical industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-Chloro-4-nitroimidazole is used as a chemical intermediate for the preparation of antitubercular nitroimidazoles. These antitubercular agents are essential in the development of medications to treat tuberculosis, a severe and widespread bacterial infection.
Used in Oncology:
In the field of oncology, 2-Chloro-4-nitroimidazole serves as a radiosensitizer for hypoxic cells. Radiosensitizers are compounds that enhance the sensitivity of cancer cells to radiation therapy, making it more effective in destroying tumor cells, particularly those with low oxygen levels that are often more resistant to treatment. This application can improve the outcomes of cancer patients undergoing radiation therapy.

InChI:InChI=1/C3H2ClN3O2/c4-3-5-1-2(6-3)7(8)9/h1H,(H,5,6)

Upstream product

• 65902-59-2 2-bromo-4-nitro-1H-imidazole 
• 16265-04-6 2-chloro-1H-imidazole 
• 542-76-7 3-Chloropropionitrile 
• 5213-49-0 2,4-dinitro-1H-imidazole 
• 683276-67-7 2-chloro-5-iodo-4-nitroimidazole 
• 683276-47-3 2-bromo-1-methoxymethyl-4-nitroimidazole 

Downstream Products

• 86072-07-3 2-chloro-1-methyl-5-nitroimidazole 
• 63634-21-9 2-chloro-1-methyl-4-nitro-1H-imidazole 
• 92918-23-5 1-(2-Chloro-5-nitro-imidazol-1-yl)-propan-2-ol 
• 92918-22-4 1-(2-Chloro-4-nitro-imidazol-1-yl)-propan-2-ol 
• 73332-79-3 2-methyl-5-nitro-2,3-dihydro-imidazo[2,1-b]oxazole 
• 681490-95-9 (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-nitrobenzoyloxy)]-propyl-4-nitroimidazole 
• 681490-93-7 2-chloro-1-{[(2R)-2-methyloxiran-2-yl]methyl}-4-nitro-1H-imidazole 
• 943610-79-5 1-[3-(tert-butyl-dimethyl-silanyloxy)-2-(2-chloro-4-nitro-imidazol-1-ylmethyl)-propyl]-4-(4-trifluoromethoxy-phenyl)-piperazine 
• 1188337-65-6 1-(4-bromo-phenyl)-2-(2-chloro-4-nitro-imidazol-1-yl)-ethanone 
• 1188337-68-9 butyric acid (R)-3-{4-[2-(2-chloro-4-nitro-imidazol-1-yl)-acetyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester 
• 943610-74-0 C₁₈H₂₆ClN₃O₃Si 
• 1253202-36-6 (S)-3-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-(4-(trifluoro-methoxy)benzyloxy)propyl 4-methoxybenzoate 
• 1263188-33-5 1-(but-3-en-1-yl)-2-chloro-4-nitro-1H-imidazole 

Relevant articles and documents

PROCESS FOR PRODUCTION OF 2-CHLORO-4-NITROIMIDAZOLE DERIVATIVES

An improved process for preparing 2-chloro-4-nitroimidazole derivatives which are useful intermediates in the preparation of an anti-tuberculosis drug is provided. The process may comprise the step of chlorinating nitroimidazoles with a chlorinating agent and an activating agent to give 2-chloro-4-nitroimidazole derivatives.

Preparation of 2-chloro-4-nitro imidazole method (by machine translation)

The invention discloses a method for preparing 2-chloro-4-nitroimidazole. The method comprises the following steps of reacting aminoacetaldehyde acetal with S-methyl-iso-thiourea sulphate to synthesise 2-aminoimidazole sulphate, and then performing diazotization reaction on 2-aminoimidazole sulphate and sodium nitrite; then performing chlorination reaction on a reactant obtained from the former step and cuprous chloride to obtain 2-chloro-imidazole; and finally performing nitration reaction with nitric acid to obtain 2-chloro-4-nitroimidazole. The synthesis method disclosed by the invention is capable of avoiding rearrangement and transposition, is moderate in reaction conditions, less in pollution, and easily realizes industrialized production.

Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: In vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation

The nitroimidazole scaffold has attracted great interest in the last decade, which ultimately led to the discovery of the successful drug Delamanid for multi-drug resistant tuberculosis (MDR-TB). Herein, we report medicinal chemistry on a 6-nitro-2,3-dihy