3'-BROMO-4'-HYDROXYACETOPHENONE Chemical Properties

Melting point:

111.0 to 115.0 °C

Boiling point:

315.9±27.0 °C(Predicted)

Density 

1.586±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

6.63±0.18(Predicted)

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

HS Code 

2914790090

3'-BROMO-4'-HYDROXYACETOPHENONE Usage And Synthesis

Preparation

Preparation by diazotization of 5-amino-3-bromo-2- hydroxyacetophenone, followed by hydrolysis of the obtained diazonium salt (50%).

Synthesis

2-Bromophenol (1.16 mL, 10.0 mmol) was dissolved in carbon disulfide (10 mL) and stirred under cooling in an ice-salt bath. Subsequently, anhydrous aluminum chloride (2.7 g, 20.0 mmol) was added in batches, followed by slow dropwise addition of acetyl chloride (0.754 mL, 11.0 mmol). The reaction mixture was maintained under stirring conditions for 1 hour and then refluxed overnight. Upon completion of the reaction, the mixture was quenched by adding a mixture of 1 M hydrochloric acid and ice to the mixture. The mixture was extracted using dichloromethane (3 times) and after combining the organic phases, it was dried and concentrated with anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (eluent: 20% ethyl acetate/hexane to 40% ethyl acetate/hexane gradient elution) to afford the target product 3-bromo-4-hydroxyacetophenone (2.28 g, 53% yield).

References

[1] Journal of Medicinal Chemistry, 1980, vol. 23, # 7, p. 738 - 744
[2] Patent: WO2004/62661, 2004, A1. Location in patent: Page/Page column 27

3'-BROMO-4'-HYDROXYACETOPHENONE(1836-06-2)Related Product Information

• 4'-Hydroxyacetophenone