2-Bromo-1-methyl-1H-imidazole

Base Information

• Chemical Name: 2-Bromo-1-methyl-1H-imidazole
• CAS No.: 16681-59-7
• Molecular Formula: C4H5 Br N2
• Molecular Weight: 161.001
• Hs Code.: 29332990
• European Community (EC) Number: 627-485-7
• DSSTox Substance ID: DTXSID00378317
• Nikkaji Number: J420.207D
• Wikidata: Q72447151
• ChEMBL ID: CHEMBL305538
• Mol file: 16681-59-7.mol

Synonyms:Imidazole,2-bromo-1-methyl- (8CI); 2-Bromo-1-methyl-1H-imidazole;2-Bromo-1-methylimidazole; 2-Bromo-N-methylimidazole

Chemical Property of 2-Bromo-1-methyl-1H-imidazole

Chemical Property:

• Refractive Index: n20/D 1.5440(lit.)
• Boiling Point: 172 ºC
• PKA: 3.83±0.25(Predicted)
• Flash Point: 110 ºC
• PSA: 17.82000
• Density: 1.649
• LogP: 1.18260
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 159.96361
• Heavy Atom Count: 7
• Complexity: 66.7

Purity/Quality:

98% ^*data from raw suppliers

2-Bromo-1-methyl-1H-imidazole ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 22-38-41
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C=CN=C1Br
• Uses: 2-Bromo-1-methylimidazole is used in in pharmaceuticals, drug candidates, ligands for transition metal catalysts and other molecular functional materials. 2-Bromo-1-methyl-1H-imidazole can be used in the synthesis of the following:N-(4-methoxyphenyl)-1-methyl-1H-imidazol-2-amine via C-N coupling with p-anisidine1,2-bis[2-methyl-5-(1-methyl-1H-imidazol-2-yl)-3-thienyl]-cyclopentene, a ligand which can form bimetallic platinum(II) complex with potent cytotoxic activity

Technology Process of 2-Bromo-1-methyl-1H-imidazole

There total 3 articles about 2-Bromo-1-methyl-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: 71.0%

1-methyl-1H-imidazole (616-47-7) → 2-bromo-1-methyl-1H-imidazole (16681-59-7)

Guidance literature:

1-methyl-1H-imidazole; With n-butyllithium; In diethyl ether; at -100 ℃; for 2h; Inert atmosphere;

With carbon tetrabromide; In diethyl ether; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.3987/COM-18-S(T)94

Reference yield: 46.0%

→ 2-bromo-1-methyl-1H-imidazole (16681-59-7)

Guidance literature:

Reference yield:

1-methyl-1,3-dihydro-imidazole-2-thione (60-56-0,223768-14-7,4708-61-6) → 2-bromo-1-methyl-1H-imidazole (16681-59-7)

Guidance literature:

With copper(I) bromide; In chloroform; acetonitrile; at 20 ℃;

DOI:10.1039/c1dt11327e

upstream raw materials:

1-methyl-1H-imidazole

1-methyl-1,3-dihydro-imidazole-2-thione

Downstream raw materials:

2,5-dibromo-1-methyl-1H-imidazole

1-(1-methyl-1H-imidazol-2-yl)piperazine

4-(1-methyl-1H-imidazol-2-yl)benzonitrile

Refernces

• 1、 Lobana, Tarlok S.,Sultana, Razia,Butcher, Ray J.. "A Sandmeyer type reaction for bromination of 2-mercapto-1-methyl- imidazoline (N2C4H6S) into 2-bromo-1-methyl- imidazole (N2C4H5Br) in presence of copper(i) bromide". . p. 11382 - 11384. Retrieved 2011.
• 2、 Oh, Chan Seok,Lee, Chil Won,Lee, Jun Yeob. "Simple heteroatom engineering for tuning the triplet energy of organometallic host materials for red, green and blue phosphorescent organic light-emitting diodes". . p. 3875 - 3877. Retrieved 2013.
• 3、 -. "1,5,7-TRISUBSTITUTED ISOQUINOLINE DERIVATIVES, PREPARATION THEREOF, AND USE THEREOF IN MEDICINES". Paragraph 0250-0251; 0291-0292. . Retrieved 2020/08/30.
• 4、 Lampl, Martin,Laus, Gerhard,Wurst, Klaus,Kahlenberg, Volker,Gelbrich, Thomas,Nerdinger, Sven,Huppertz, Hubert,Schottenberger, Herwig. "2-Functionalized derivatives of 2-bromo-1,3-dimethylimidazole". . p. 1116 - 1127. Retrieved 2019/07/31.