2-Bromo-6-chloroquinoline

Base Information

• Chemical Name: 2-Bromo-6-chloroquinoline
• CAS No.: 891842-50-5
• Molecular Formula: C9H5BrClN
• Molecular Weight: 242.502
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID20591642
• Wikidata: Q72453540
• Mol file: 891842-50-5.mol

Synonyms:2-bromo-6-chloroquinoline;891842-50-5;2-bromo-6-chloro-quinoline;SCHEMBL3304612;2-bromanyl-6-chloranyl-quinoline;DTXSID20591642;CZRQPBUNCHUQAN-UHFFFAOYSA-N;MFCD09261123;AKOS015904359;SB69453;CS-0225349;EN300-1234953;A843085

Chemical Property of 2-Bromo-6-chloroquinoline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• Boiling Point: 328.087 °C at 760 mmHg
• PKA: -0.31±0.43(Predicted)
• Flash Point: 152.222 °C
• PSA: 12.89000
• Density: 1.673 g/cm³
• LogP: 3.65070
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 240.92939
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Bromo-6-chloroquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=N2)Br)C=C1Cl

Technology Process of 2-Bromo-6-chloroquinoline

There total 3 articles about 2-Bromo-6-chloroquinoline 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%

6-chloroquinolin-2(1H)-oney (1810-67-9) → 2--bromo-6--chloroquinoline (891842-50-5)

Guidance literature:

With tetrabutylammomium bromide; phosphorus pentoxide; In xylene; at 220 ℃; for 0.277778h; microwave irradiation;

Reference yield: 72.0%

6-chloroquinoline N-oxide (6563-10-6) → 2--bromo-6--chloroquinoline (891842-50-5)

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

Reference yield:

6-chloroquinoline (612-57-7) → 2--bromo-6--chloroquinoline (891842-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 14 h / 0 - 20 °C

2.1: tetrabutylammomium bromide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 20 °C / Inert atmosphere

With tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ol3034675

upstream raw materials:

6-chloroquinolin-2(1H)-oney

6-chloroquinoline

6-chloroquinoline N-oxide

Downstream raw materials:

6-chloro-2-phenylquinoline

C₁₈H₁₃ClF₄N₂O

C₁₈H₁₀ClF₄NO

C₁₇H₈ClF₄NO

Refernces

• 1、 Wengryniuk, Sarah E.,Weickgenannt, Andreas,Reiher, Christopher,Strotman, Neil A.,Chen, Ke,Eastgate, Martin D.,Baran, Phil S.. "Regioselective bromination of fused heterocyclic N-oxides". . p. 792 - 795. Retrieved 2013/04/10.