8-Bromoquinoline Chemical Properties

Melting point:

58-59 °C

Boiling point:

112-113 °C/0.5 mmHg (lit.)

Density 

1.594 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.672(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

form 

Liquid After Melting

pka

2.33±0.17(Predicted)

Specific Gravity

1.594

color 

Clear yellow to yellow-brown

Sensitive 

Light Sensitive

InChI

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

InChIKey

PIWNKSHCLTZKSZ-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2Br)C=CC=1

CAS DataBase Reference

16567-18-3(CAS DataBase Reference)

NIST Chemistry Reference

Quinoline, 8-bromo-(16567-18-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29334900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

8-Bromoquinoline Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

8-Bromoquinoline may be used in the following studies:

• Synthesis of 8-(dimesitylboryl)quinolone (ambiphilic molecule).
• Direct synthesis of 5H-pyrido[3,2,1-ij]quinolin-3-one, via palladium catalyzed coupling reaction with acrolein.
• Preparation of 8-(1-hydroxyethyl)quinolone.
• Preparation of 8-quinolylcyclopentadienyl metal complexes, via reaction with zincated cyclopentadienyl derivatives of Fe, Mn and Re in the presence of bis(triphenylphosphine)palladium(0).
• Synthesis of n,n′-biquinolines by a coupling reaction using tris(triphenylphosphine)nickel(0) and a zerovalent pyridine-nickel complex.

General Description

8-Bromoquinoline is a quinolone derivative. It is widely employed for the synthesis of dyes, food colors, pharmaceutical reagents, pH indicators and in various industrial processes. Its molecule bears a pyridyl group. It undergoes direct heteroarylation reaction with various heteroaromatic compounds in the presence of a palladium catalyst to afford polyheteroaromatic derivatives.

Synthesis

GENERAL PROCEDURE: A 1N HCl solution (82.5 mL) was added to a round-bottomed flask containing o-bromoaniline (~1 mmol). Acrolein diethyl acetal (2.5 mmol) was then added. The reaction mixture was refluxed at 111 °C for 24 hours. After completion of the reaction, it was cooled to room temperature and neutralized to pH 7-8 with solid Na2CO3. The product was extracted with dichloromethane (3 x 100 mL), the organic layers were combined and dried over anhydrous Na2SO4. The solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was purified by column chromatography using a solvent mixture of hexane and ethyl acetate (or 15% ethyl acetate/cyclohexane and methanol) as eluent to give the target product 8-bromoquinoline.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6436 - 6439

8-Bromoquinoline(16567-18-3)Related Product Information

• Ethoxyquin
• Isoquinoline
• Quinolinic acid
• 8-Hydroxyquinoline
• QUINOLINE SULPHATE
• Quinclorac
• Quinhydrone
• 8-BROMOQUINOLINE-4-OL
• 2-BROMOQUINOLINE 98%
• 8-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID
• 8-BROMO-4-CHLOROQUINOLINE
• 8-BROMO-4-CHLORO-2-METHYLQUINOLINE
• 8-BROMO-5-NITROQUINOLINE
• ETHYL 8-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLATE
• 4-Bromoquinoline-3-boronic acid, 97%
• 4-bromoquinoline-6-carboxylic acid
• 4-Amino-3-bromoquinoline
• 8-BROMO-4-HYDROXY-2-METHYLQUINOLINE