6-Bromo-2-chloroquinoline

Base Information

• Chemical Name: 6-Bromo-2-chloroquinoline
• CAS No.: 1810-71-5
• Molecular Formula: C9H5 Br Cl N
• Molecular Weight: 242.502
• Hs Code.: 2933499090
• European Community (EC) Number: 675-964-4
• DSSTox Substance ID: DTXSID60512472
• Nikkaji Number: J2.669.163J
• Wikidata: Q72453530
• Mol file: 1810-71-5.mol

Synonyms:6-bromo-2-chloroquinoline

Chemical Property of 6-Bromo-2-chloroquinoline

Chemical Property:

• Vapor Pressure: 0.000429mmHg at 25°C
• Melting Point: 148-150℃
• Boiling Point: 325.7°Cat760mmHg
• PKA: -0.48±0.43(Predicted)
• Flash Point: 150.8°C
• PSA: 12.89000
• Density: 1.673g/cm³
• LogP: 3.65070
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in Chloroform and Methanol
• XLogP3: 3.4
• 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:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=N2)Cl)C=C1Br
• Uses: It is used as a pharmaceutical intermediate.

Technology Process of 6-Bromo-2-chloroquinoline

There total 14 articles about 6-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: 100.0%

6-bromo-2-quinolone (1810-66-8) → 6-bromo-2-chloroquinoline (1810-71-5)

Guidance literature:

With trichlorophosphate; Reflux;

DOI:10.1021/acsmedchemlett.9b00309

Reference yield: 79.0%

6-bromoquinoline-N-oxide (6563-11-7) → 6-bromo-2-chloroquinoline (1810-71-5)

Guidance literature:

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

DOI:10.1002/ejoc.201501567

Reference yield:

4-bromo-aniline (106-40-1) → 6-bromo-2-chloroquinoline (1810-71-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / pyridine / CH₂Cl₂ / 1.5 h / 25 °C

2: 83 percent / conc. H₂SO₄ / 3 h / 25 °C

3: 83 percent / POCl₃ / 1 h / Heating

With pyridine; sulfuric acid; trichlorophosphate; In dichloromethane;

DOI:10.1016/S0223-5234(00)01167-3

upstream raw materials:

6-bromo-2-quinolone

6-bromo-3,4-dihydro-1H-quinolin-2-one

4-bromo-2-iodoaniline

methyl (E)-3-(2-amino-5-bromophenyl)prop-2-enoate

Downstream raw materials:

2-methoxy-6-bromoquinoline

6-o-tolylquinolin-2-amine

6-(2-chlorophenyl)quinolin-2-amine

6-(3-chlorophenyl)quinolin-2-amine

Refernces

Sequential and selective Buchwald-Hartwig amination reactions for the controlled functionalization of 6-bromo-2-chloroquinoline: Synthesis of ligands for the Tec Src homology 3 domain

10.1021/jo801808r

The research focuses on the development of new 6-heterocyclic substituted 2-aminoquinolines using Buchwald-Hartwig amination reactions. These compounds are designed to have increased binding affinity for the Tec Src Homology 3 (SH3) domain, a protein-protein interaction domain that is a valuable target for therapeutic agents. The study explores the selective amination of an aryl bromide in the presence of an activated heteroaryl chloride, optimizing reaction conditions to achieve cross-coupling with various cyclic amines. Key chemicals involved in the research include 6-bromo-2-chloroquinoline as the starting material, palladium catalysts such as Pd(OAc)2, various phosphine ligands like CataCXium A (16), and bases like KOtBu and NaOtBu. The reactions also utilize a range of cyclic amines as coupling partners to introduce different heterocyclic substituents at the 6-position of the quinoline ring. The study further investigates the use of lithium bis(trimethylsilyl)amide (LHMDS) as an ammonia equivalent for the amination process to convert 2-chloroquinolines to 2-aminoquinolines, providing an improved method over traditional approaches. The binding affinity of the synthesized compounds with the Tec SH3 domain is assessed through NMR chemical shift perturbation analysis, revealing that the new ligands exhibit enhanced binding affinities compared to the lead compound, 2-aminoquinoline.