4-Bromoisoquinoline Chemical Properties

Melting point:

40-43 °C (lit.)

Boiling point:

280-285 °C (lit.)

Density 

1.5617 (rough estimate)

refractive index 

1.6641 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform, Methanol

pka

3.30±0.10(Predicted)

form 

Crystalline Solid

color 

White to light beige

BRN 

114431

InChI

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

InChIKey

SCRBSGZBTHKAHU-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1532-97-4(CAS DataBase Reference)

NIST Chemistry Reference

Isoquinoline, 4-bromo-(1532-97-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

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

Safety Statements 

26-37/39-36/37/39-22-36

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:4-Bromoisoquinoline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromoisoquinoline Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

Shows selective inhibition of cAMP-dependent protein kinase

Preparation

2-Alkynyl benzyl azides could smoothly undergo an electrocyclic reaction catalyzed by palladium to afford either 4-bromoisoquinoline or 4-bromoisquinolones selectively under different conditions. 4-Bromoisoquinoline was synthesised in the presence of PdBr2/CuBr2/LiBr in MeCN, and 4-bromoisoquinolone was selectively produced with PdBr2/CuBr2/HOAc in CH2ClCH2Cl[1].

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 10, p. 409, 1973 DOI: 10.1002/jhet.5570100326

Synthesis

Synthesis of Intermediate-12: 3-Bromoisoquinoline: To a stirred solution of isoquinoline (24 g, 186 mmol) in acetic acid (50 mL) was slowly added N-bromosuccinimide (NBS, 36.2 g, 204.6 mmol) at room temperature. The reaction mixture was heated to 100 °C and the reaction was stirred at this temperature overnight. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by fast column chromatography (eluent: 5% ethyl acetate/hexane) to give 4-bromoisoquinoline (9.2 g, 23.8% yield) as an oil.

References

[1] Hong-ping Zhang, Hongzhan Xiao, Hong‐Yan Li. “A Selective Synthesis of 4-Bromoisoquinoline and 4-Bromoisquinolone.” Journal of Chemical Research-s (2013).

4-Bromoisoquinoline(1532-97-4)Related Product Information

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