6-Bromo-1-chloroisoquinoline Chemical Properties

Boiling point:

349.5±22.0 °C(Predicted)

Density 

1.673

storage temp. 

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

pka

1.48±0.38(Predicted)

form 

powder

color 

Light yellow to yellow

InChI

InChI=1S/C9H5BrClN/c10-7-1-2-8-6(5-7)3-4-12-9(8)11/h1-5H

InChIKey

VOAHGGQULSSGQW-UHFFFAOYSA-N

SMILES

C1(Cl)C2=C(C=C(Br)C=C2)C=CN=1

Safety Information

Hazard Codes 

T

Risk Statements 

25-38-41

Safety Statements 

26-45

RIDADR 

UN2811

HS Code 

2933499090

6-Bromo-1-chloroisoquinoline Usage And Synthesis

Chemical Properties

Yellow solid

Uses

6-Bromo-1-chloroisoquinoline has been used as a reactant in the preparation of phenylimidazoles as Smoothened antagonists.

Synthesis

N-oxide 6-bromoisoquinoline (1.82 g, 8.12 mmol) was dissolved in dry DCM (80 mL), POCl3 (1.12 ml, 1.5 eq) was added dropwise at RT. The reaction was heated to 45°C for 2 hours. After cooling down the reaction to RT, DCM and excessive POCl3 were removed under the vacuum. The crude was re-dissolved into 100mL DCM and was washed by saturated Na2CO3, water and brine. The separated organic layer was dried over Na2SO4, and concentrated to give brown solid. The crude was purified by flash column using 2% MeOH in DCM to get the pale yellow solid 6-Bromo-1-chloroisoquinoline.

References

[1] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[2] Patent: WO2013/185353, 2013, A1. Location in patent: Page/Page column 27
[3] Patent: WO2014/165232, 2014, A1. Location in patent: Paragraph 0202; 0203
[4] Patent: US2015/119387, 2015, A1. Location in patent: Paragraph 0203; 0204
[5] Patent: JP2017/95498, 2017, A. Location in patent: Paragraph 0122; 0123

6-Bromo-1-chloroisoquinoline(205055-63-6)Related Product Information

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