2-BROMO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID METHYL ESTER

Base Information

• Chemical Name: 2-BROMO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID METHYL ESTER
• CAS No.: 120781-02-4
• Molecular Formula: C6H7 Br N2 O2
• Molecular Weight: 219.038
• Hs Code.: 2933290090
• Mol file: 120781-02-4.mol

Synonyms:2-BROMO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID METHYL ESTER

Chemical Property of 2-BROMO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID METHYL ESTER

Chemical Property:

• Vapor Pressure: 0.000408mmHg at 25°C
• Refractive Index: 1.589
• Boiling Point: 316.5°Cat760mmHg
• PKA: 1.04±0.25(Predicted)
• Flash Point: 145.2°C
• PSA: 44.12000
• Density: 1.67g/cm³
• LogP: 0.96920
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Methyl2-Bromo-1-methyl-1H-imidazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2-Bromo-1-methyl-1H-imidazole-5-carboxylate is used for the synthesis of anti-tuberculosis drug PA-824 against M. tuberculosis.

Technology Process of 2-BROMO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID METHYL ESTER

There total 5 articles about 2-BROMO-3-METHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID METHYL ESTER 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: 83.0%

methyl 1-methyl-1H-imidazole-5-carboxylate (17289-20-2) → 2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (120781-02-4)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 60 ℃; for 50h;

DOI:10.1055/s-1988-27702

Reference yield: 49.0%

→ 2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (120781-02-4)

Guidance literature:

Reference yield:

1-methyl-1H-imidazole-5-carboxylic acid (41806-40-0) → 2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (120781-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / SOCl₂ / 24 h / Heating

2: 83 percent / NBS / AIBN / CCl₄ / 50 h / 60 °C

With N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;

DOI:10.1055/s-1988-27702

upstream raw materials:

methyl 1-methyl-1H-imidazole-5-carboxylate

1-methyl-1H-imidazole-5-carboxylic acid

1-methyl-1H-imidazole-4,5-dicarboxylic acid

1-methyl-4,5-dicyanoimidazole

Downstream raw materials:

methyl 1-methyl-2-phenyl-1H-imidazole-5-carboxylate

methyl 1-methyl-2-[4-(trifluoromethoxy)phenyl]-1H-imidazole-5-carboxylate

methyl 2-(3-fluoro-4-methoxyphenyl)-1-methyl-1H-imidazole-5-carboxylate

methyl 2-(4-cyanophenyl)-1-methyl-1H-imidazole-5-carboxylate

Refernces

• 1、 -. "NOVEL PYRIDAZINE COMPOUNDS FOR CONTROLLING INVERTEBRATE PESTS". Page/Page column 125. . Retrieved 2019/08/06.
• 2、 Emmerich, Juliette,Van Koppen, Chris J.,Burkhart, Jens L.,Hu, Qingzhong,Siebenbürger, Lorenz,Boerger, Carsten,Scheuer, Claudia,Laschke, Matthias W.,Menger, Michael D.,Hartmann, Rolf W.. "Lead Optimization Generates CYP11B1 Inhibitors of Pyridylmethyl Isoxazole Type with Improved Pharmacological Profile for the Treatment of Cushing's Disease". supporting information. p. 5086 - 5098. Retrieved 2017/06/28.