4-Nitroimidazole

Base Information

• Chemical Name: 4-Nitroimidazole
• CAS No.: 3034-38-6
• Deprecated CAS: 196413-24-8,88054-21-1,932779-11-8,88054-21-1,932779-11-8
• Molecular Formula: C3H3N3O2
• Molecular Weight: 113.076
• Hs Code.: 2933.29
• European Community (EC) Number: 221-224-7
• NSC Number: 50359
• UNII: Y8U32AZ5O7
• DSSTox Substance ID: DTXSID9062803
• Nikkaji Number: J2.909.230C,J2.169E
• Metabolomics Workbench ID: 63443
• ChEMBL ID: CHEMBL135599
• Mol file: 3034-38-6.mol

Synonyms:4-nitroimidazole;5-nitroimidazole

Chemical Property of 4-Nitroimidazole

Chemical Property:

• Appearance/Colour: white to light yellow powder
• Melting Point: 303 °C (dec.)(lit.)
• Refractive Index: 1.4264 (estimate)
• Boiling Point: 404.8 °C at 760 mmHg
• PKA: 8.31±0.10(Predicted)
• Flash Point: 198.6 °C
• PSA: 74.50000
• Density: 1.552 g/cm³
• LogP: 0.84110
• Storage Temp.: Store below +30°C.
• Solubility.: 0.40g/l
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 113.022526347
• Heavy Atom Count: 8
• Complexity: 99.2

Purity/Quality:

99% ^*data from raw suppliers

4-Nitro-1H-imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C,F
• Hazard Codes: Xn,C,F
• Statements: 20/21/22-36/37/38-22-34-11
• Safety Statements: 26-36/37-37/39-45-36/37/39-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=N1)[N+](=O)[O-]
• Uses: Metronidazole (M338880) derivative, an antibacterial in the treatment of rosacea and inflammatory bowel disease. 4-Nitroimidazole was used in a study to investigate the catalytic efficiency of heterocyclic compounds in the peroxyoxalate chemiluminescence reaction using bis(2,4,6-trichlorophenyl)oxalate as reagent.

Technology Process of 4-Nitroimidazole

There total 25 articles about 4-Nitroimidazole 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: 96.1%

1H-imidazole (288-32-4) → 1H-4(5)-nitroimidazole (3034-38-6)

Guidance literature:

With sulfuric acid; nitric acid; at 60 ℃; Temperature; Flow reactor;

Reference yield: 92.4%

4-amino-1H-imidazole (4919-03-3) → 1H-4(5)-nitroimidazole (3034-38-6)

Guidance literature:

With oxone; In water; at 35 ℃; for 16h; Temperature;

Reference yield: 87.0%

aniline (62-53-3) + 4-nitro-1-(o-nitrobenzenesulfonyl)imidazole → 2-Nitrobenzenesulfonamide (5455-59-4) + 1H-4(5)-nitroimidazole (3034-38-6) + 1-phenyl-4-nitro-1H-imidazole (41384-83-2)

Guidance literature:

In methanol; water; at 65 - 70 ℃; for 2h;

upstream raw materials:

1H-imidazole

5⁽⁴⁾-nitro-1⁽³⁾H-imidazole-4⁽⁵⁾-carboxylic acid

1,4-dinitro-1H-imidazole

aniline

Downstream raw materials:

1-methyl-4-nitro-1H-imidazole

1-methyl-5-nitro-1H-imidazole

4-amino-1H-imidazole

glycine

Refernces

• 1、 Bulusu, S.,Damavarapu, R.,Autera, J. R.,Behrens, R., Jr.,Minier, L. M.,et al.. "Thermal Rearrangement of 1,4-Dinitroimidazole to 2,4-Dinitroimidazole: Characterization and Investigation of the Mechanism by Mass Spectrometry and Isotope Labeling". . p. 5009 - 5015. Retrieved 1995.
• 2、 -. "Preparation method of 4-nitroimidazole". Paragraph 0019-0027. . Retrieved 2021/07/09.
• 3、 -. "Method for preparing 4, 5-dinitroimidazole by adopting microchannel reactor". Page/Page column 0042-0057; 0070-0072; 0076-0077. . Retrieved 2019/06/27.