2,4-Dinitroimidazole

Base Information

• Chemical Name: 2,4-Dinitroimidazole
• CAS No.: 5213-49-0
• Molecular Formula: C3H2N4O4
• Molecular Weight: 158.073
• European Community (EC) Number: 829-496-4
• NSC Number: 342704
• DSSTox Substance ID: DTXSID70200136
• Nikkaji Number: J49.327I
• Wikidata: Q11309544
• ChEMBL ID: CHEMBL3230461
• Mol file: 5213-49-0.mol

Synonyms:2,4-Dinitroimidazole;5213-49-0;2,4-DINITRO-1H-IMIDAZOLE;2,5-dinitro-1H-imidazole;2,4-DINITRO-3H-IMIDAZOLE;2,5-Dinitroimidazole;1H-Imidazole, 2,4-dinitro-;Imidazole, 2,4-dinitro-;Imidazole, 2,5-dinitro-;KA 121;NSC 342704;Imidazole,4-dinitro-;Imidazole,5-dinitro-;1H-Imidazole,4-dinitro-;SCHEMBL64072;WLN: T5M CNJ BNW DNW;WLN: T5M CNJ BNW ENW;2,4-Dinitro-1H-imidazole #;CHEMBL3230461;SCHEMBL12441774;DTXSID70200136;AMY10071;BCP24315;C3-H2-N4-O4;NSC342704;STK506070;AKOS005172151;AKOS015966685;AKOS025394725;NSC-342704;AS-37813;LS-78531;A7661;BB 0260742;FT-0660855;EN300-174721;J-507379

Chemical Property of 2,4-Dinitroimidazole

Chemical Property:

• Vapor Pressure: 2.99E-10mmHg at 25°C
• Melting Point: 271-271.5 °C
• Refractive Index: 1.676
• Boiling Point: 503.1 °C at 760 mmHg
• PKA: 3.14±0.10(Predicted)
• Flash Point: 258.1 °C
• PSA: 120.32000
• Density: 1.867g/cm³
• LogP: 1.27250
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 158.00760456
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,4-Dinitro-1H-imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC(=N1)[N+](=O)[O-])[N+](=O)[O-]
• Uses: 2,4-Dinitro-1H-imidazole is a reagent that can be used to synthesize (S)-PA 824 (P122500), which is a novel anti-tuberculosis drug.

Technology Process of 2,4-Dinitroimidazole

There total 6 articles about 2,4-Dinitroimidazole 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: 94.0%

1,4-dinitro-1H-imidazole (19182-81-1) → 2,4-dinitro-1H-imidazole (5213-49-0)

Guidance literature:

In chlorobenzene; at 125 ℃;

DOI:10.1016/j.tca.2021.179097

Reference yield:

1,4-dinitro-1H-imidazole (19182-81-1) → 1H-4(5)-nitroimidazole (3034-38-6) + 2,4,5-trinitroimidazole (24079-73-0) + 2,4-dinitro-1H-imidazole (5213-49-0)

Guidance literature:

at 91 ℃; for 18h; Product distribution; Mechanism; isothermal decomposition;

DOI:10.1021/j100014a022

Reference yield:

1-(2,4-Dinitro-imidazol-1-yl)-propan-2-one (131394-05-3) → 2,4-dinitro-1H-imidazole (5213-49-0)

Guidance literature:

With sulfuric acid; nitric acid; at 0 - 20 ℃; for 48h;

DOI:10.1002/cplu.201800305

upstream raw materials:

1,4-dinitro-1H-imidazole

1H-4⁽⁵⁾-nitroimidazole

1-(2,4-Dinitro-imidazol-1-yl)-propan-2-one

Downstream raw materials:

2-methyl-5-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

2-Butyl-2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

2-Isopropoxymethyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

1-(2,4-dinitro-imidazol-1-yl)-propan-2-ol

Refernces

• 1、 Raina, Gaurav,Kannaboina, Prakash,Mupparapu, Nagaraju,Raina, Sushil,Ahmed, Qazi Naveed,Das, Parthasarathi. "Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions". . p. 2134 - 2147. Retrieved 2019/02/27.
• 2、 -. "Synthesis and purification method of 2, 4-dinitroimidazole". Paragraph 0042; 0043; 0044. . Retrieved 2017/02/28.