3-Bromo-2-methylimidazo[1,2-a]pyridine

Base Information

• Chemical Name: 3-Bromo-2-methylimidazo[1,2-a]pyridine
• CAS No.: 4805-70-3
• Molecular Formula: C8H7BrN2
• Molecular Weight: 211.061
• European Community (EC) Number: 819-375-4
• DSSTox Substance ID: DTXSID00428124
• Wikidata: Q82240907
• Mol file: 4805-70-3.mol

Synonyms:3-bromo-2-methylimidazo[1,2-a]pyridine;4805-70-3;MFCD02251329;SCHEMBL792006;DTXSID00428124;QYPXIXIHSALTNV-UHFFFAOYSA-N;AMY15928;AS-8130;SY204687;3-bromo-2-methyl-imidazo[1,2-a]pyridine;CS-0084386;EN300-247493;F51878;J-511886

Chemical Property of 3-Bromo-2-methylimidazo[1,2-a]pyridine

Chemical Property:

• Melting Point: 73 °C
• Boiling Point: 1.6 g/cm³
• PKA: 6.05±0.10(Predicted)
• PSA: 17.30000
• Density: 1.60±0.1 g/cm3(Predicted)
• LogP: 2.40520
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 209.97926
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

98%min ^*data from raw suppliers

3-bromo-2-methylimidazo[1,2-a]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N2C=CC=CC2=N1)Br

Technology Process of 3-Bromo-2-methylimidazo[1,2-a]pyridine

There total 9 articles about 3-Bromo-2-methylimidazo[1,2-a]pyridine 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: 95.0%

2-methylimidazo[1,2-a]pyridine (934-37-2) → 3-bromo-2-methylimidazo[1,2-a]pyridine (4805-70-3)

Guidance literature:

With sodium carbonate; pyridinium hydrobromide perbromide; In N,N-dimethyl-formamide; at 25 - 43 ℃; for 0.5h; regioselective reaction; Sonication; Schlenk technique; Green chemistry;

DOI:10.1055/s-0040-1707856

Reference yield: 90.0%

2-aminopyridine (504-29-0) + 1-bromoacetone (598-31-2) → 3-bromo-2-methylimidazo[1,2-a]pyridine (4805-70-3)

Guidance literature:

With tert.-butylhydroperoxide; In ethyl acetate; at 90 ℃; for 3h;

DOI:10.1039/c9ra06724h

Reference yield: 42.0%

dihydroxy-methyl-borane (13061-96-6) + 2-iodo-3-bromoimidazo[1,2-a]pyridine → 3-bromo-2-methylimidazo[1,2-a]pyridine (4805-70-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 120 ℃; for 1h; regioselective reaction; Microwave irradiation;

DOI:10.1039/c7ob00624a

upstream raw materials:

N-Bromosuccinimide

2-methylimidazo[1,2-a]pyridine

2-amino-1-(prop-2-yn-1-yl)pyridin-1-ium bromide

2-aminopyridine

Downstream raw materials:

N-(2-chloro-5-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

3-(diphenylphosphorothioyl)-2-methylimidazo[1,2-a]pyridine hydrochloride

3-(diphenylphosphoryl)-2-methylimidazo[1,2-a]pyridine hydrochloride

(2-methylimidazo[1,2-a]pyridin-3-yl)diphenylmethanol

Refernces

• 1、 Lee, Ju Hui,Jung, Hye Im,Kim, Dae Young. "Visible light-mediated photocatalytic bromination of 2-arylimidazo[1,2-a]pyridines using CBr4 as bromine source". supporting information. p. 197 - 206. Retrieved 2019/12/03.
• 2、 Liu, Yanpeng,Lu, Lixue,Zhou, Haipin,Xu, Feijie,Ma, Cong,Huang, Zhangjian,Xu, Jinyi,Xu, Shengtao. "Chemodivergent synthesis of: N -(pyridin-2-yl)amides and 3-bromoimidazo[1,2- a] pyridines from α-bromoketones and 2-aminopyridines". . p. 34671 - 34676. Retrieved 2019/11/13.