2-CHLORO-5-NITROANISOLE Chemical Properties

Melting point:

81-83°C

Boiling point:

287.3±20.0 °C(Predicted)

Density 

1.366±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate

form 

Solid

color 

Brown

CAS DataBase Reference

1009-36-5(CAS DataBase Reference)

EPA Substance Registry System

2-Chloro-5-nitroanisole (1009-36-5)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/37/38-51-22-36/38

Safety Statements 

26-36/37/39-28

Hazard Note 

Irritant

HS Code 

29093090

2-CHLORO-5-NITROANISOLE Usage And Synthesis

Chemical Properties

White Solid

Uses

2-Chloro-5-nitroanisole (cas# 1009-36-5) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of 2-chloro-5-nitroanisole from 2-methoxy-4-nitroaniline: In an agate mortar, camphorsulfonic acid (1.5 mmol), tert-butyl nitrite (3.0 mmol), benzyltriethylammonium chloride (2.5 mmol), and a catalytic amount of copper(II) chloride (1 mol%) were mixed with 2-methoxy-4-nitroaniline (1.25 mmol) were mixed. The mixture was vigorously ground for 15-20 min until nitrogen release stopped completely. Upon completion of the reaction (confirmed by thin layer chromatography), the crude product was treated according to the treatment of aryl bromide reaction and purified by column chromatography using hexane/dichloromethane as eluting solvent. The physical properties and 1H NMR data of the resulting product were consistent with those of commercially available analytically pure samples.

References

[1] Tetrahedron, 2013, vol. 69, # 16, p. 3511 - 3517
[2] Environmental Toxicology and Chemistry, 2001, vol. 20, # 7, p. 1381 - 1389
[3] Tetrahedron Letters, 2010, vol. 51, # 51, p. 6769 - 6771
[4] Tetrahedron, 2010, vol. 66, # 37, p. 7418 - 7422
[5] Chemische Berichte, 1899, vol. 32, p. 2623

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