3-benzyl-6-bromo-2-chloroquinoline

Base Information

• Chemical Name: 3-benzyl-6-bromo-2-chloroquinoline
• CAS No.: 654655-68-2
• Molecular Formula: C16H11BrClN
• Molecular Weight: 332.627
• Hs Code.: 2933499090
• Mol file: 654655-68-2.mol

Synonyms:Quinoline,6-bromo-2-chloro-3-(phenylmethyl);6-bromo-2-chloro-3-(phenylmethyl)-quinoline;3-benzyl-6-bromo-2-chloro-quinoline;

Chemical Property of 3-benzyl-6-bromo-2-chloroquinoline

Chemical Property:

• Melting Point: 111-112℃
• Boiling Point: 435.9±40.0 °C(Predicted)
• PKA: -0.42±0.50(Predicted)
• PSA: 12.89000
• Density: 1.482±0.06 g/cm3(Predicted)
• LogP: 5.24150
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3-Benzyl-6-bromo-2-chloroquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Benzyl-6-bromo-2-chloroquinoline is an intermediate in the synthesis of (αS,βR)-Bedaquiline (B119540), which is a diarylquinoline derivative that acts as a mycobacterial inhibitor. Bedaquiline shows promise as potential drug in the treatment of tuberculosis.

Technology Process of 3-benzyl-6-bromo-2-chloroquinoline

There total 10 articles about 3-benzyl-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: 97.0%

3-benzyl-6-bromo-1H-quinolin-2-one (924633-09-0) → 3-benzyl-6-bromo-2-chloro-quinoline (654655-68-2)

Guidance literature:

With trichlorophosphate; In toluene; at 120 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.10.053

Reference yield: 71.0%

acetonitrile (75-05-8,26809-02-9) + N-(4-bromophenyl)-3-phenylpropanamide (316146-27-7) → 3-benzyl-6-bromo-2-chloro-quinoline (654655-68-2)

Guidance literature:

With trichlorophosphate; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

DOI:10.1016/j.cclet.2015.04.013

Reference yield: 67.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + N-(4-bromophenyl)-3-phenylpropanamide (316146-27-7) → 3-benzyl-6-bromo-2-chloro-quinoline (654655-68-2)

Guidance literature:

With trichlorophosphate; at 10 - 80 ℃;

upstream raw materials:

3-benzyl-6-bromo-1H-quinolin-2-one

2-[(4-bromo-phenylamino)-phenyl-methyl]-acrylic acid ethyl ester

ethyl 2-(hydroxy(phenyl)methyl)propenoate

ethyl 2-(acetoxy(phenyl)methyl)acrylate

Downstream raw materials:

3-benzyl-6-bromo-2-methoxyquinoline

intermediate compound 4

C₁₆H₁₂BrNS

C₂₂H₁₆BrNO