5-Chloro-1-methyl-4-nitroimidazole

Base Information

• Chemical Name: 5-Chloro-1-methyl-4-nitroimidazole
• CAS No.: 4897-25-0
• Molecular Formula: C4H4ClN3O2
• Molecular Weight: 161.548
• Hs Code.: 2933290090
• European Community (EC) Number: 225-521-2
• NSC Number: 7852
• UNII: P917JW98BD
• DSSTox Substance ID: DTXSID00197646
• Nikkaji Number: J2.221G
• Wikidata: Q27286392
• ChEMBL ID: CHEMBL1610328
• Mol file: 4897-25-0.mol

Synonyms:1-methyl- 4-nitro-5-chloroimidazoles;1-methyl-5-chloro-4-nitroimidazole;5-chloro-1-methyl-4-nitroimidazole;CMNI;NSC 7852

Chemical Property of 5-Chloro-1-methyl-4-nitroimidazole

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 4.08E-05mmHg at 25°C
• Melting Point: 148-150 °C(lit.)
• Refractive Index: 1.648
• Boiling Point: 362.3 °C at 760 mmHg
• PKA: -1.37±0.61(Predicted)
• Flash Point: 172.9 °C
• PSA: 63.64000
• Density: 1.65 g/cm³
• LogP: 1.50490
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 160.9992041
• Heavy Atom Count: 10
• Complexity: 148

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-1-methyl-4-nitroimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC(=C1Cl)[N+](=O)[O-]
• Description: 5-Chloro-1-methyl-4-nitroimidazole is an imidazole derivative. It is useful in the rapid mix experiments to investigate the mechanism of anomalous radiosensitization of mammalian cells. It can also be used in the synthesis of 5-aryl-1-methyl-4-nitroimidazoles, via Suzuki coupling with arylboronic acids, catalyzed by dichlorobis-(triphenylphosphine) palladium (II), K2CO3 and tetrabutylammonium bromide. 5-Chloro-1-methyl-4-nitroimidazole is an intermediate in azathioprine synthesis, also present in the end product. It induced contact dermatitis in a man working on azathioprine synthesis. Cross reactivity is possible with imidazoles tioconazole, and econazole.
• Uses: 5-Chloro-1-methyl-4-nitroimidazole (CMNI) is suitable for use in the rapid mix experiments to investigate the mechanism of anomalous radiosensitization of mammalian cells by CMNI. It may be used in the synthesis of 5-aryl-1-methyl-4-nitroimidazoles, via Suzuki coupling with arylboronic acids, catalyzed by dichlorobis-(triphenylphosphine)palladium(II), K2CO3 and tetrabutylammonium bromide.

Technology Process of 5-Chloro-1-methyl-4-nitroimidazole

There total 8 articles about 5-Chloro-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: 91.0%

N-methyl-5-chloroimidazole (872-49-1) → 5-chloro-1-methyl-4-nitroimidazole (4897-25-0)

Guidance literature:

With sulfuric acid; nitric acid; In water; Heating;

DOI:10.1016/j.bmcl.2006.11.087

Reference yield: 74.0%

1-methyl-4,5-dinitro-1H-imidazole (19183-15-4) → 5-chloro-1-methyl-4-nitroimidazole (4897-25-0)

Guidance literature:

With hydrogenchloride; for 3h; Heating;

Reference yield: 41.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 4-chloro-5-nitroimidazole (57531-38-1) → 5-chloro-1-methyl-4-nitroimidazole (4897-25-0) + 4-chloro-1-methyl-5-nitro-1H-imidazole (4897-31-8)

Guidance literature:

In diethyl ether; Ambient temperature;

upstream raw materials:

diazomethane

4-chloro-5-nitroimidazole

dimethyl sulfate

4⁽⁵⁾-Chloro-5⁽⁴⁾-nitroimidazol

Downstream raw materials:

1-Methyl-4-nitro-5-piperidinoimidazole

1-Methyl-4-nitro-5-(N-phenylpiperazino)-imidazole

5-Methoxy-1-methyl-4-nitroimidazole

1-methyl-4-nitro-5-imidazolyl 2-chloro-6-methylphenyl sulfide

Refernces

• 1、 -. "4,5-DIAMINOIMIDAZOLES AS NOVEL DEVELOPER-TYPE OXIDATION DYE PRECURSORS". Paragraph 0277-0280. . Retrieved 2017/10/22.
• 2、 Kiselyov, Alexander S.,Piatnitski, Evgueni L.,Samet, Alexander V.,Kisliy, Victor P.,Semenov, Victor V.. "ortho-Substituted azoles as selective and dual inhibitors of VEGF receptors 1 and 2". . p. 1369 - 1375. Retrieved 2007/10/03.