2-Bromo-1,5-dimethyl-1H-imidazole

Base Information

• Chemical Name: 2-Bromo-1,5-dimethyl-1H-imidazole
• CAS No.: 235426-31-0
• Molecular Formula: C5H7BrN2
• Molecular Weight: 175.028
• Hs Code.: 2933290090
• European Community (EC) Number: 691-788-0
• DSSTox Substance ID: DTXSID70428398
• Nikkaji Number: J1.101.975G
• Mol file: 235426-31-0.mol

Synonyms:2-Bromo-1,5-dimethyl-1H-imidazole;235426-31-0;2-bromo-1,5-dimethylimidazole;SCHEMBL3325158;DTXSID70428398;CQONRJOUCSSFLX-UHFFFAOYSA-N;1,5-Dimethyl-2-bromo-1H-imidazole;MFCD06659902;AKOS006343257;AB26586;AT22512;PS-3654;CS-0213130;FT-0687393;2-Bromo-1,5-dimethyl-1H-imidazole, AldrichCPR;A854926;Q-103104

Chemical Property of 2-Bromo-1,5-dimethyl-1H-imidazole

Chemical Property:

• Vapor Pressure: 0.0181mmHg at 25°C
• Melting Point: 40-42 °C
• Refractive Index: 1.589
• Boiling Point: 253.6 °C at 760 mmHg
• PKA: 4.17±0.25(Predicted)
• Flash Point: 107.1 °C
• PSA: 17.82000
• Density: 1.58 g/cm³
• LogP: 1.49100
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 173.97926
• Heavy Atom Count: 8
• Complexity: 86.5

Purity/Quality:

98%min ^*data from raw suppliers

2-Bromo-1,5-dimethyl-1H-imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(N1C)Br

Technology Process of 2-Bromo-1,5-dimethyl-1H-imidazole

There total 3 articles about 2-Bromo-1,5-dimethyl-1H-imidazole 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: 38.0%

2-bromo-5-methyl-1H-imidazole (23328-88-3) + methyl trifluoromethanesulfonate (333-27-7) → 2-bromo-1,5-dimethyl-1H-imidazole (235426-31-0)

Guidance literature:

C₃H₂BrIN₂; With triethylamine; benzenesulfonyl chloride; In acetonitrile; for 8h; Inert atmosphere;

methyl trifluoromethanesulfonate; In acetonitrile; for 24h; Inert atmosphere;

With N-n-butyl-N-methylamine; In acetonitrile; at 80 ℃; regioselective reaction; Inert atmosphere; Heating;

DOI:10.1021/jo401978b

Reference yield: 34.0%

2-bromo-5-methyl-1H-imidazole (23328-88-3) + methyl iodide (74-88-4) → 2-bromo-1,5-dimethyl-1H-imidazole (235426-31-0)

Guidance literature:

2-bromo-5-methyl-1H-imidazole; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;

Reference yield: 27.0%

1,2-dimethylimidazole (10447-93-5) → 2-bromo-1,5-dimethyl-1H-imidazole (235426-31-0)

Guidance literature:

With bromocyane; In acetonitrile; Ambient temperature;

DOI:10.1071/C98105

upstream raw materials:

1,2-dimethylimidazole

2-bromo-5-methyl-1H-imidazole

methyl trifluoromethanesulfonate

methyl iodide

Downstream raw materials:

N-[4-chloro-3-(1,5-dimethylimidazol-2-yl)phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide

4-chloro-3-(1,5-dimethylimidazol-2-yl)aniline

N-[3-(1,5-dimethylimidazol-2-yl)-4-methyl-phenyl]-2-methyl-6-(trifluoromethyl)pyridine-3-carboxamide

Refernces

• 1、 Van Den Berge, Emilie,Robiette, Raphael. "Development of a regioselective N-methylation of (benz)imidazoles providing the more sterically hindered isomer". . p. 12220 - 12223. Retrieved 2014/01/06.