2-Bromo-4-chloroanisole Chemical Properties

Melting point:

28.6-29.1°C

Boiling point:

122/20mm

Density 

1.625

vapor pressure 

8.7Pa at 25℃

refractive index 

1.5850-1.5890

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Liquid

Specific Gravity

1.61

color 

Clear colorless to pale yellow

CAS DataBase Reference

60633-25-2(CAS DataBase Reference)

NIST Chemistry Reference

2-Bromo-4-chloroanisole(60633-25-2)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-51-22

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29093090

MSDS

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2-Bromo-4-chloroanisole Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

2-Bromo-4-chloroanisole has been used as a reactant in the preparation of naphthyl phenyl ethers as nonnucleoside HIV-1 reverse transcriptase inhibitors.

Synthesis

General procedure for the synthesis of 2-bromo-4-chloroanisole from 2-bromo-4-chlorophenol and iodomethane: In a 250 mL round-bottomed flask, 2-bromo-4-chlorophenol (16.94 g, 81.6 mmol, 1.0 eq.) was dissolved in acetone (160 mL), and iodomethane (6.10 mL, 98 mmol, 1.2 eq.), potassium carbonate (12 g), and water (4 mL). The reaction mixture was heated to reflux for 3 h. After cooling to room temperature, most of the volatiles were removed under reduced pressure. The residue was poured into water (140 mL) and extracted with ethyl acetate (3 x 150 mL). The organic phases were combined, washed with brine (1 x 100 mL), dried (K2CO3), filtered through a pad of diatomaceous earth and concentrated to give a clear oil. Purification by short-range distillation (80°-85 °C, 1 Torr) afforded 17.74 g (98% yield) of 2-bromo-4-chloroanisole as a clear liquid. 2-bromo-4-chloroanisole was characterized by NMR hydrogen spectroscopy (400 MHz, acetone-d6) with the following data: δ 7.53 (d, J = 2.5 Hz, 1H); 7.24 (dd, J = 9.7, 2.5 Hz. 1H); 6.81 (d, J = 9.7 Hz, 1H); 3.88 (s, 3H).

References

[1] Angewandte Chemie - International Edition, 2008, vol. 47, # 27, p. 5067 - 5070
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 14, p. 4220 - 4226
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6443 - 6448
[4] Angew. Chem., 2014, vol. 126, # 25, p. 6561 - 6566
[5] Patent: US5688808, 1997, A

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