1-Methyl-4-nitroimidazole

Base Information

• Chemical Name: 1-Methyl-4-nitroimidazole
• CAS No.: 3034-41-1
• Molecular Formula: C4H5 N3 O2
• Molecular Weight: 127.103
• Hs Code.: 2933290090
• European Community (EC) Number: 802-213-1
• UNII: Z31100A55O
• DSSTox Substance ID: DTXSID50184425
• Nikkaji Number: J86.858B,J2.341.584D
• Wikidata: Q27149662
• ChEMBL ID: CHEMBL3544543
• Mol file: 3034-41-1.mol

Synonyms:1-Methyl-4-nitroimidazole;3034-41-1;1-Methyl-4-nitro-1H-imidazole;1H-Imidazole, 1-methyl-4-nitro-;Imidazole, 1-methyl-4-nitro-;BRN 0123533;AI3-51824;UNII-Z31100A55O;CHEBI:80615;MFCD00159683;Z31100A55O;5-23-04-00486 (Beilstein Handbook Reference);3-methyl-5-nitroimidazole;SCHEMBL174098;METRONIDAZOLE IMPURITY I;CHEMBL3544543;DTXSID50184425;CL2229;STK760074;AKOS000601578;AM85708;CS-W018929;NCGC00340396-01;1-Methyl-4-nitro-3-azonia-1H-imidazole;AC-23143;DS-17161;LS-78790;SY041755;EU-0052121;FT-0698197;M3171;AB01332166-02;A876217;Q27149662

Chemical Property of 1-Methyl-4-nitroimidazole

Chemical Property:

• Vapor Pressure: 0.000352mmHg at 25°C
• Melting Point: 133-134℃
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 328.9°Cat760mmHg
• PKA: 0.32±0.61(Predicted)
• Flash Point: 152.7°C
• PSA: 63.64000
• Density: 1.44g/cm³
• LogP: 0.85150
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 127.038176411
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

1-Methyl-4-nitroimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(N=C1)[N+](=O)[O-]
• Uses: 1-Methyl-4-nitroimidazole is a moiety of Azathioprine (A803350) and is predicted to have mutagenic potential.

Technology Process of 1-Methyl-4-nitroimidazole

There total 9 articles about 1-Methyl-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: 59.0%

Dimethyl oxalate (553-90-2) + 1H-4(5)-nitroimidazole (3034-38-6) → 1-methyl-4-nitro-1H-imidazole (3034-41-1) + 1-methyl-5-nitro-1H-imidazole (3034-42-2)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; Heating;

DOI:10.1016/S0040-4039(01)90086-3

Reference yield: 19.0%

1H-4(5)-nitroimidazole (3034-38-6) + dimethyl sulfate (77-78-1) → 1-methyl-4-nitro-1H-imidazole (3034-41-1) + 1-methyl-5-nitro-1H-imidazole (3034-42-2)

Guidance literature:

With sodium hydroxide;

Reference yield: 1.0%

1-methyl-1H-imidazole (616-47-7) → 1-methyl-4-nitro-1H-imidazole (3034-41-1) + 1-methyl-2,4-dinitroimidazole (5213-50-3) + 1-methyl-2,4,5-trinitroimidazole (19183-20-1) + 1-methyl-2-nitroimidazole (1671-82-5,176738-19-5)

Guidance literature:

With sulfuric acid; sulfur trioxide; nitric acid; at 110 - 120 ℃; for 2h; Product distribution / selectivity;

upstream raw materials:

1-methyl-1H-imidazole

diazomethane

diethyl ether

1H-4⁽⁵⁾-nitroimidazole

Downstream raw materials:

1-methyl-4-nitro-1H-imidazol-5-amine

1-methyl-1H-imidazole-4-amine hydrochloride

2,6-dichloro-N-(1-methyl-1H-imidazol-4-yl)pyrimidin-4-amine

1-methyl-1H-imidazol-4-amine

Refernces

• 1、 -. "Melt-cast explosive material". Page/Page column 7. . Retrieved 2008/06/13.
• 2、 Lissel, Manfred. "Reactions with Dimethyl Carbonate, 2. - N-Methylation of Imidazole and Derivatives". . p. 77 - 80. Retrieved 2007/10/02.