2-Bromo-4-methylquinoline

Base Information

• Chemical Name: 2-Bromo-4-methylquinoline
• CAS No.: 64658-04-4
• Molecular Formula: C10H8BrN
• Molecular Weight: 222.084
• Hs Code.: 2933499090
• NSC Number: 109469
• DSSTox Substance ID: DTXSID60296462
• Nikkaji Number: J2.218.610H
• Wikidata: Q72448048
• Mol file: 64658-04-4.mol

Synonyms:2-bromo-4-methylquinoline;64658-04-4;2-bromo-4-methyl-quinoline;NSC109469;4-methylquinoline bromide;SCHEMBL362901;DTXSID60296462;MFCD08705663;AKOS022176178;AM85862;DS-7646;NSC-109469;SB71587;CS-0153142;FT-0705543;EN300-339729;A867847;J-508315

Chemical Property of 2-Bromo-4-methylquinoline

Chemical Property:

• Vapor Pressure: 0.000901mmHg at 25°C
• Melting Point: 81-81.5 °C
• Refractive Index: 1.654
• Boiling Point: 313.7 °C at 760 mmHg
• PKA: 1.15±0.50(Predicted)
• Flash Point: 143.5 °C
• PSA: 12.89000
• Density: 1.488 g/cm³
• LogP: 3.30570
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 220.98401
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

98%,99% ^*data from raw suppliers

2-Bromo-4-methylquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NC2=CC=CC=C12)Br

Technology Process of 2-Bromo-4-methylquinoline

There total 5 articles about 2-Bromo-4-methylquinoline 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: 88.0%

4-methylquinolin-2-ol (607-66-9,84909-43-3) → 2-bromo-4-methyl-quinoline (64658-04-4)

Guidance literature:

With phosphorus(V) oxybromide; at 60 - 120 ℃;

DOI:10.1021/ol061364k

Reference yield: 85.0%

2,4-dibromoquinoline (20151-40-0) + methyl iodide (74-88-4) → 2-bromo-4-methyl-quinoline (64658-04-4)

Guidance literature:

2,4-dibromoquinoline; With n-butyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃;

methyl iodide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

DOI:10.1016/j.tetlet.2005.07.137

Reference yield: 51.0%

4-methylquinoline 1-oxide (4053-40-1) → 2-bromo-4-methyl-quinoline (64658-04-4)

Guidance literature:

With N,N-dimethyl-formamide; phosphorus(V) oxybromide; In dichloromethane; at 0 - 25 ℃; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2016.07.083

upstream raw materials:

4-methylquinolin-2-ol

2,4-dibromoquinoline

methyl iodide

4-methylquinoline 1-oxide

Downstream raw materials:

4-methyl-2-(4-morpholinyl)quinoline

2,2′-biquinoline-4,4′-dicarboxylic acid

4-methyl-2-phenylquinoline

4-methylquinoline-2-carbaldehyde

Refernces

• 1、 Wang, Dong,Wang, Yuxi,Zhao, Junjie,Li, Linna,Miao, Longfei,Wang, Dong,Sun, Hua,Yu, Peng. "A highly practical and convenient halogenation of fused heterocyclic N-oxides". . p. 5762 - 5768. Retrieved 2016/08/30.
• 2、 Comins, Daniel L.,Nolan, Jason M.,Bori, Ibrahim D.. "Regioselective lithium-halogen exchange and palladium-catalyzed cross-coupling reactions of 2,4-dihaloquinolines". . p. 6697 - 6699. Retrieved 2007/10/03.