5-Bromoisoquinoline Chemical Properties

Melting point:

83-87 °C (lit.)

Boiling point:

95-97°C 0,1mm

Density 

1.564±0.06 g/cm3(Predicted)

Flash point:

95-97°C/0.1mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

pka

4.39±0.13(Predicted)

color 

Yellow

BRN 

114468

InChI

InChI=1S/C9H6BrN/c10-9-3-1-2-7-6-11-5-4-8(7)9/h1-6H

InChIKey

CYJZJGYYTFQQBY-UHFFFAOYSA-N

SMILES

C1C2=C(C(Br)=CC=C2)C=CN=1

CAS DataBase Reference

34784-04-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-21/22-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29334900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Bromoisoquinoline Usage And Synthesis

Description

5-Bromoisoquinoline is a synthetic intermediate useful for pharmaceutical synthesis.

Chemical Properties

White to yellow-brown crystals

Uses

Starting material employed in palladium-catalyzed aminomethylation and amination reactions.

Synthesis Reference(s)

[1] W. Brown, A. Gouliaev. “Bromination of Isoquinoline, Quinoline, Quinazoline and Quinoxaline in Strong Acid.” ChemInform 98 1 (2002).

Synthesis

To mechanically stirred concd H2SO4 (42.5 mL) at 0 °C, isoquinoline (1; 5 mL, 42.5 mmol) was slowly added. The mixture was cooled to –25 °C, and NBS (9.83 g, 55.2 mmol) was added at such a rate that the reaction temperature was kept between –25 °C and –22 °C. The mixture was stirred at -22±1 °C for 2 h and at -18±1 °C for 3h. The mixture was then worked up as described above to give 6.16 g (72%) as a slightly off-white solid after chromatography; mp 81–82 °C. The solid was further purified by sublimation (75 °C/0.2 mmHg) to give 5-Bromoisoquinoline as a white powder[1].

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