5-Bromo-2-methylphenol Chemical Properties

Melting point:

75-80 °C

Boiling point:

144-146 °C(Press: 1.1 Torr)

Density 

1.554±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

crystals

pka

9.35±0.10(Predicted)

color 

Brown

CAS DataBase Reference

36138-76-8

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

1

HazardClass 

IRRITANT

HS Code 

29081990

5-Bromo-2-methylphenol Usage And Synthesis

Chemical Properties

Light yellow solid

Synthesis

General procedure for the synthesis of 5-bromo-2-methylphenol from 2-amino-4-bromotoluene: A solution of concentrated sulfuric acid (6 mL) in distilled water (75 mL) was added to 5-bromo-2-methylaniline (1 g, 5.38 mmol). The resulting suspension was heated to 90 °C and stirred for 4.5 hours. Subsequently, the reaction mixture was cooled to 0 °C using an ice bath and a solution of sodium nitrite (384 mg, 5.57 mmol) in water (5 mL) was slowly added at this temperature. After addition, the reaction mixture was allowed to gradually warm up to room temperature. Next, the reaction mixture was poured into a solution of concentrated sulfuric acid (6 mL) in water (75 mL) preheated to 90°C. Stirring of the reaction mixture was continued at 90 °C for 1 hour, then the heating was stopped and it was allowed to cool naturally and stand overnight. A precipitate was observed to form from the reaction mixture. The precipitate was collected by filtration, washed with water and dried in a vacuum oven to give 5-bromo-2-methylphenol as a final brown solid (510 mg, 2.73 mmol, 51% yield). The mass spectrum (ESI) showed m/z of 185 and 187 [M-H]?

References

[1] Patent: US2007/185156, 2007, A1. Location in patent: Page/Page column 8-9
[2] Patent: WO2007/63071, 2007, A1. Location in patent: Page/Page column 19
[3] Justus Liebigs Annalen der Chemie, 1913, vol. 398, p. 366
[4] Dissertation , S. 21,
[5] Journal of the Chemical Society, 1926, p. 2038

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