2-Bromoquinoline Chemical Properties

Melting point:

44-48 °C

Boiling point:

115°C/0.3mmHg(lit.)

Density 

1.564±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

0.58±0.40(Predicted)

color 

White to Light yellow

λmax

319nm(EtOH)(lit.)

InChI

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

InChIKey

QKJAZPHKNWSXDF-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2005-43-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-41-37/38-22

Safety Statements 

26-36-39-22

WGK Germany 

3

HS Code 

29339900

2-Bromoquinoline Usage And Synthesis

Chemical Properties

White powder

Synthesis

The general procedure for the synthesis of 2-bromoquinoline from 1-methyl-2-quinolone was as follows: Triphenylphosphine (1186 mg, 4.52 mmol) and dibromoisocyanuric acid (652 mg, 2.27 mmol) were sequentially added to a 50 mL round bottom flask fitted with a magnetic stirrer and a balloon (for pressure equilibrium) under nitrogen protection. The mixture was heated to 115 °C, at which point the dibromoisocyanuric acid reacted vigorously, and the reaction was continued to maintain this temperature for 10 min. Subsequently, 1-methylquinolin-2(1H)-one (239 mg, 1.50 mmol) was added to the reaction system and the temperature of the reaction was raised to 160-170°C for 16 hours. After completion of the reaction, the reaction mixture was dissolved in dichloromethane and alkalized with triethylamine. Purification was carried out by silica gel column chromatography with hexane-ethyl acetate (6:1, v/v) as eluent to finally obtain 2-bromoquinoline (244 mg, 78% yield). 2-bromoquinoline was a yellow oil, and its 1H-NMR (CDCl3) data were as follows: δ 7.51 (1H, d, J = 8.4 Hz), 7.51-8.20 (4H, m), 7.98 ( 1H, d, J = 8.4Hz).

References

[1] Heterocycles, 2015, vol. 91, # 7, p. 1445 - 1454

2-Bromoquinoline(2005-43-8)Related Product Information

• Quinhydrone
• 8-Hydroxyquinoline
• Quinolinic acid
• Quinoline Yellow
• Ethoxyquin
• Quinclorac
• Isoquinoline
• quinolinium hydrogen sulphate
• 2-BROMOQUINOLINE-4-CARBOXYLIC ACID
• 2-BROMOQUINOLINE-3-BORONIC ACID
• 2-BROMOQUINOLINE-4-CARBOXALDEHYDE
• 3-AMINO-2-BROMOQUINOLINE
• 2-Bromo-6-methylquinoline
• 2-BROMO-4-CHLOROQUINOLINE
• 2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE
• 2,3-DIBROMOQUINOLINE
• 4-AMINO-2-BROMOQUINOLINE
• 8-BROMOQUINOLINE