4-BROMO-2-METHYLANISOLE Chemical Properties

Melting point:

66-69 °C(lit.)

Boiling point:

124-125°C 25mm

Density 

1.378±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

124-125°C/25mm

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow

BRN 

208224

CAS DataBase Reference

14804-31-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29093090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-BROMO-2-METHYLANISOLE Usage And Synthesis

Chemical Properties

colorless to light yellow liquid

Uses

4-Bromo-2-methylanisole may be used in the synthesis of 4-isopropyl-2-methylphenol and 4-methoxy-3-methylphenol.

General Description

4-Bromo-2-methylanisole can be prepared by the bromination of o-methylanisole (2-methylanisole). It can also be prepared via reaction between 1-butyl-3-methylimidazolium tribromide [(Bmim)Br₃] and an activated aromatic compound. It participates as a substrate for the a-arylation of sulphonamide in a study.

Synthesis

General procedure for the synthesis of 2-methyl-4-bromoanisole from 2-methylanisole: In a dry 45 mL reaction tube equipped with a magnetic stirrer (note: air was not removed from the reaction tube), 1 mL of [Bmim]NO3, 0.5 mmol of 2-methylanisole and 0.25 mmol of Br2 were added. The reaction tube was then sealed and the reaction was carried out at 80 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was terminated by the addition of 3 mL of water. The target product 2-methyl-4-bromoanisole was extracted with dichloromethane (3 x 10 mL). The reaction mixture was analyzed by gas chromatography (GC) to determine the GC yield of the product. In another parallel experiment, the product was purified by column chromatography and structurally characterized using 1H NMR and 13C NMR.

References

[1] Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1068 - 1077
[2] Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1068 - 1077
[3] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[4] Chemistry - A European Journal, 2015, vol. 21, # 34, p. 11976 - 11979
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 603 - 604

4-BROMO-2-METHYLANISOLE(14804-31-0)Related Product Information

• (4-bromo-2-methylphenyl)methanol
• 4-Bromo-2,6-dimethylaniline
• 4-Bromo-3-fluorobenzonitrile
• 4-Bromo-3-fluorobenzaldehyde
• 4-Bromo-2-chlorobenzonitrile
• 4-Bromo-3-methylphenol
• 4-Bromo-3-fluorobenzoic acid
• 4-Bromo-2-fluorobenzotrifluoride
• 4-Bromo-2-methyl-benzaldehyde
• 4-Bromo-2-fluoroanisole
• 4-BROMO-3-CHLOROPHENOL
• 4-Bromo-2-methylpyridine
• 5-BROMO-2-METHOXYBENZYL ALCOHOL
• Solvent Red 43
• 5-BROMO-2-METHOXYCINNAMIC ACID
• 6-BROMOCOUMARIN-3-CARBOXYLIC ACID
• Acid Red 87
• 5-Bromo-2-chlorobenzoic acid