3-Bromo-2-chloroquinoline

Base Information

• Chemical Name: 3-Bromo-2-chloroquinoline
• CAS No.: 101870-60-4
• Molecular Formula: C9H5BrClN
• Molecular Weight: 242.502
• Hs Code.: 2933499090
• European Community (EC) Number: 829-672-0
• DSSTox Substance ID: DTXSID60459131
• Nikkaji Number: J1.939.260K
• Wikidata: Q82282769
• Mol file: 101870-60-4.mol

Synonyms:3-BROMO-2-CHLOROQUINOLINE;101870-60-4;QUINOLINE, 3-BROMO-2-CHLORO-;MFCD08457743;3-bromo-2-chloro-quinoline;SCHEMBL1767846;DTXSID60459131;2-CHLORO-3-BROMOQUINOLINE;RWWUFTQVKMNRQN-UHFFFAOYSA-N;BEA87060;AKOS005257081;PB20265;AS-33662;CS-0051485;FT-0682317;EN300-258136;W-204433

Chemical Property of 3-Bromo-2-chloroquinoline

Chemical Property:

• Vapor Pressure: 0.00105mmHg at 25°C
• Melting Point: 96-98 °C
• Refractive Index: 1.68
• Boiling Point: 311.2 °C at 760 mmHg
• PKA: -2.14±0.50(Predicted)
• Flash Point: 142 °C
• PSA: 12.89000
• Density: 1.673 g/cm³
• LogP: 3.65070
• Storage Temp.: Inert atmosphere,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

3-Bromo-2-chloroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=N2)Cl)Br

Technology Process of 3-Bromo-2-chloroquinoline

There total 5 articles about 3-Bromo-2-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: 91.0%

potassium (2-chloroquinolin-3-yl)trifluoroborate → 3-bromo-2-chloro-quinoline (101870-60-4)

Guidance literature:

With tetra-N-butylammonium tribromide; In tetrahydrofuran; water; at 20 ℃; for 12h; chemoselective reaction;

DOI:10.1021/ol9027144

Reference yield: 89.0%

3-bromoquinolin-2-one (939-16-2) → 3-bromo-2-chloro-quinoline (101870-60-4)

Guidance literature:

With trichlorophosphate; In acetonitrile; at 20 ℃; for 3h; Reflux;

DOI:10.1016/j.tet.2013.08.019

Reference yield: 84.0%

3-bromoquinoline N-oxide (22615-00-5) → 3-bromo-2-chloro-quinoline (101870-60-4)

Guidance literature:

With trichloroacetonitrile; triphenylphosphine; In toluene; at 115 ℃; for 4h; regioselective reaction; Sealed tube;

DOI:10.1002/ejoc.201501567

upstream raw materials:

3-bromoquinoline N-oxide

3-bromoquinolin-2-one

3-bromoquinoline

Downstream raw materials:

3-bromo-2-iodoquinoline

6H-quinindoline

3-bromo-2-methoxyquinoline

Refernces

• 1、 Sabol, Mark R.,Owen, John M.,Erickson, W. Randal. "A novel and efficient synthesis of 2,3-dichloroquinoline". . p. 427 - 432. Retrieved 2000.
• 2、 Priebbenow, Daniel L.,Barbaro, Lisa,Baell, Jonathan B.. "New synthetic approaches towards analogues of bedaquiline". supporting information. p. 9622 - 9628. Retrieved 2016/10/25.
• 3、 Yao, Min-Liang,Kabalka, George W.,Blevins, David W.,Reddy, Marepally Srinivasa,Yong, Li. "Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide". experimental part. p. 3738 - 3743. Retrieved 2012/06/30.