2-BROMO-5-NITROANISOLE Chemical Properties

Melting point:

99-103 °C

Boiling point:

302.1±22.0 °C(Predicted)

Density 

1.640±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Water Solubility 

Insoluble in water

form 

Crystalline Powder

color 

Light brown

λmax

324nm(EtOH)(lit.)

BRN 

2520496

CAS DataBase Reference

77337-82-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

24/25-26

Hazard Note 

Irritant

HS Code 

29093090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-BROMO-5-NITROANISOLE Usage And Synthesis

Chemical Properties

light brown crystalline powder

Synthesis

General procedure for the synthesis of 2-bromo-5-nitroanisole from 2-methoxy-4-nitroaniline: a catalytic amount of copper bromide (1 mol%) was added to a solution of 2-methoxy-4-nitroaniline (2.5 mmol) in acetonitrile (30 ml), followed by camphorsulfonic acid (3.0 mmol), sodium nitrite or tert-butyl nitrite (3.0 mmol), and tetrabutylammonium bromide (5.0 mmol). The reaction mixture was stirred at 60°C for 24 h (Tables 1 and 2). Nitrogen release was observed immediately during the reaction. After completion of the reaction (confirmed by β-naphthol test and thin layer chromatography), the solvent was removed using a rotary evaporator. The residue was washed with water and extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Finally, purification by column chromatography using a hexane/dichloromethane solvent mixture as eluent gave the pure product 2-bromo-5-nitroanisole. The physical properties and 1H NMR data of the product were consistent with the commercially available analytically pure sample.

References

[1] Tetrahedron, 2013, vol. 69, # 16, p. 3511 - 3517
[2] Tetrahedron, 2010, vol. 66, # 37, p. 7418 - 7422
[3] Tetrahedron Letters, 2010, vol. 51, # 51, p. 6769 - 6771
[4] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[5] Journal of the American Chemical Society, 1935, vol. 57, p. 1592,1594

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