2-Chloro-4-nitro-1H-imidazole

Base Information

• Chemical Name: 2-Chloro-4-nitro-1H-imidazole
• CAS No.: 57531-37-0
• Molecular Formula: C3H2ClN3O2
• Molecular Weight: 147.521
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID90206150
• Nikkaji Number: J1.579.080F
• Wikidata: Q72455836
• Mol file: 57531-37-0.mol

Synonyms:57531-37-0;2-Chloro-4-Nitroimidazole;2-CHLORO-4-NITRO-1H-IMIDAZOLE;2-Chloro-5-nitro-1H-imidazole;2-chloro-5-nitroimidazole;1H-Imidazole, 2-chloro-4-nitro-;MFCD03419295;nitrochloroimidazole;2-chloro-4 -nitroimidazole;SCHEMBL58560;DTXSID90206150;BBL104426;STK505561;AKOS000321249;AKOS015833831;AC-6400;CS-W018201;PS-4408;SB14865;SY011512;A8204;AM20100411;FT-0650343;EN300-134613;Q-102349

Chemical Property of 2-Chloro-4-nitro-1H-imidazole

Chemical Property:

• Vapor Pressure: 3.45E-06mmHg at 25°C
• Melting Point: 216-217 °C
• Refractive Index: 1.631
• Boiling Point: 386.8 °C at 760 mmHg
• PKA: 5.65±0.10(Predicted)
• Flash Point: 187.7 °C
• PSA: 74.50000
• Density: 1.74 g/cm³
• LogP: 1.49450
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 146.9835540
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

98% ^*data from raw suppliers

2-Chloro-4-nitroimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC(=N1)Cl)[N+](=O)[O-]
• General Description: 2-Chloro-4-nitroimidazole is a key intermediate in the synthesis of PA-824, an antituberculosis drug candidate, where it serves as a safer alternative to hazardous precursors like 2,4-dinitroimidazole. Its inclusion in the streamlined four-step synthesis contributes to improved efficiency, cost-effectiveness, and safety, supporting scalable production of PA-824 for tuberculosis treatment in high-burden regions.

Technology Process of 2-Chloro-4-nitro-1H-imidazole

There total 10 articles about 2-Chloro-4-nitro-1H-imidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.6%

2-chloro-5-iodo-4-nitroimidazole (683276-67-7) → 2-chloro-4-nitro-1H-imidazole (57531-37-0)

Guidance literature:

With hydrogen; triethylamine; platinum(IV) oxide; In ethanol; at 20 ℃; for 2h;

Reference yield: 92.0%

2,4-dinitro-1H-imidazole (5213-49-0) → 2-chloro-4-nitro-1H-imidazole (57531-37-0)

Guidance literature:

With hydrogenchloride; In water; at 90 - 95 ℃;

DOI:10.1039/c5ob00054h

Reference yield: 87.3%

2-chloro-1H-imidazole (16265-04-6) → 2-chloro-4-nitro-1H-imidazole (57531-37-0)

Guidance literature:

2-chloro-1H-imidazole; With sulfuric acid; at 20 ℃; for 0.5h;

With sulfuric acid; nitric acid; at 45 - 110 ℃; for 1h;

upstream raw materials:

2-bromo-4-nitro-1H-imidazole

2-chloro-1H-imidazole

3-Chloropropionitrile

2,4-dinitro-1H-imidazole

Downstream raw materials:

2-chloro-1-methyl-5-nitroimidazole

2-chloro-1-methyl-4-nitro-1H-imidazole

1-(2-Chloro-5-nitro-imidazol-1-yl)-propan-2-ol

1-(2-Chloro-4-nitro-imidazol-1-yl)-propan-2-ol

Refernces

A concise and convergent synthesis of PA-824

10.1021/jo1015807

The research focuses on the development of a concise and convergent four-step synthesis method for PA-824, a promising antituberculosis drug candidate. The purpose of this study was to improve upon the existing synthetic route used for large-scale production of PA-824, addressing concerns related to cost, safety, and efficiency. The new approach offers significant improvements by utilizing a safe alternative to the explosive 2,4-dinitroimidazole and a functionalized pseudosymmetrical glycidol derivative. Key chemicals used in the synthesis include (R)-3-chloro-1,2-propanediol, p-methoxybenzoyl chloride, 4-(trifluoromethoxy)benzyl alcohol, 2-chloro-4-nitroimidazole, and potassium hydroxide. The synthesis process culminates in the production of PA-824 with high yield and enantiomeric excess, demonstrating the potential for kilogram-scale production. The conclusions of the research highlight the efficiency, simplicity, and safety of the new synthetic method, which is crucial for the future production and distribution of affordable TB treatments, especially in developing regions where the disease is most prevalent.