3-benzyl-6-bromo-2-chloroquinoline Chemical Properties

Melting point:

111-112℃

Boiling point:

435.9±40.0 °C(Predicted)

Density 

1.482±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.42±0.50(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C16H11BrClN/c17-14-6-7-15-12(10-14)9-13(16(18)19-15)8-11-4-2-1-3-5-11/h1-7,9-10H,8H2

InChIKey

UGXUDVNBDYIJHJ-UHFFFAOYSA-N

SMILES

N1C2C(=CC(Br)=CC=2)C=C(CC2=CC=CC=C2)C=1Cl

3-benzyl-6-bromo-2-chloroquinoline Usage And Synthesis

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.

References

[1] Tetrahedron, 2007, vol. 63, # 2, p. 451 - 460
[2] Patent: WO2009/91324, 2009, A1. Location in patent: Page/Page column 20-21

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