8-Bromomethylquinoline Chemical Properties

Melting point:

81 °C

Boiling point:

321.9±17.0 °C(Predicted)

Density 

1.518±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Dichloromethane

form 

Solid

pka

3.85±0.17(Predicted)

color 

White

BRN 

119140

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

34-22-52-41

Safety Statements 

26-36/37/39-45-24/25-22-39

RIDADR 

3261

WGK Germany 

3

Hazard Note 

Corrosive

HazardClass 

IRRITANT

HS Code 

29334900

8-Bromomethylquinoline Usage And Synthesis

Uses

8-Bromomethylquinoline is an intermediate in synthesizing 8-Quinolinemethanamine Dihydrochloride (Q700700), which is a salt form of 8-Quinolinemethanamine. 8-Quinolinemethanamine is used in the preparation of quinazolinone derivatives as anti-tumor agents.

Chemical Properties

Light yellow powder

Uses

8-Bromomethylquinoline is an intermediate in synthesizing 8-Quinolinemethanamine Dihydrochloride (Q700700), which is a salt form of 8-Quinolinemethanamine. 8-Quinolinemethanamine is used in the preparation of quinazolinone derivatives as anti-tumor agents.

Synthesis

To a pre-dried 300 mL three-necked flask under nitrogen atmosphere were added 8-methylquinoline (10.0 g, 69.8 mmol), benzoyl peroxide (0.843 g, 3.49 mmol) and cyclohexane (150 mL). Under stirring conditions, N-bromosuccinimide (13.6 g, 76.8 mmol) was added in batches. The reaction mixture was refluxed for 10 hours. After completion of the reaction, the reaction mixture was filtered. The filtrate was washed sequentially with saturated aqueous sodium bicarbonate (3 x 100 mL) and brine (100 mL) and then dried with anhydrous sodium sulfate. Subsequently, the solvent was removed by vacuum evaporation. Finally, recrystallization was carried out using ether and hexane to give the light brown solid product 8-bromomethylquinoline (7.1 g, 46% yield).

References

[1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 1 - 9
[2] Journal of Organometallic Chemistry, 1994, vol. 484, # 1-2, p. C8 - C9
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1995, # 13, p. 2289 - 2296
[4] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 4, p. 477 - 479
[5] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 2109 - 2116

8-Bromomethylquinoline(7496-46-0)Related Product Information

• Bromotrimethylsilane
• BROMOPENTAMETHYLBENZENE
• Cyclohexylmethyl bromide
• Benzyl bromide
• Methyl 4-(bromomethyl)benzoate
• 4-methylquinoline
• Quinoline
• Methyl bromide
• ALPHA,ALPHA,ALPHA-TRIBROMOQUINALDINE
• 8-(Dibromomethyl)quinoline ,99.5%
• 3-BROMOMETHYLQUINOLINE
• 4-Bromomethyl Carbostryill
• 2-Bromomethylquinoline
• 4-Bromomethyl-1,2-dihydroquinoline-2-one
• 6-bromomethylquinoline(HBr)
• Quinoline, 6-(bromomethyl)- (6CI,9CI)
• 2,3-BIS(BROMOMETHYL)QUINOXALINE
• 6-bromo-8-(bromomethyl)quinoline