6-Bromo-8-fluoroquinoline

6-Bromo-8-fluoroquinoline Property

Melting point:

104-106°C

Boiling point:

294.9±20.0 °C(Predicted)

Density 

1.647±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

crystalline powder

pka

1.14±0.20(Predicted)

color 

Pale yellow

InChI

InChI=1S/C9H5BrFN/c10-7-4-6-2-1-3-12-9(6)8(11)5-7/h1-5H

InChIKey

DDCOYWOYIUEOHQ-UHFFFAOYSA-N

SMILES

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

Safety

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933499090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

6-Bromo-8-fluoroquinoline Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 6-bromo-8-fluoroquinoline from 4-bromo-2-fluoroaniline and glycerol: 3-nitrobenzenesulfonic acid sodium salt (0.48 g, 2.132 mmol) and glycerol (0.516 ml, 7.06 mmol) were added to a concentrated H2SO4 (0.63 ml, 11.82 mmol) and H2O (0.48 ml, 26.6 mmol) solution to form a thick gray suspension. The mixture was heated to 110°C. 4-Bromo-2-fluoroaniline was added in batches over a period of 10 min, during which the temperature was raised to 95°C. The reaction mixture was then heated to 140 °C and stirred overnight. Upon completion of the reaction, the reaction mixture was cooled, poured into water and the pH was adjusted with ammonia to 7. The brown precipitate formed was collected by filtration and partially dried. The resulting solid (0.63 g) was purified by fast column chromatography to afford 6-bromo-8-fluoroquinoline (0.4 g, 1.77 mmol, 88% yield).

References

[1] Patent: WO2009/50204, 2009, A1. Location in patent: Page/Page column 15; 48-49
[2] Patent: WO2018/116072, 2018, A1. Location in patent: Page/Page column 97; 98
[3] Patent: CN105968115, 2016, A. Location in patent: Paragraph 0449-0451
[4] Patent: WO2010/20363, 2010, A1. Location in patent: Page/Page column 131-132
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 4066 - 4084