4-Iodo-2-nitroanisole Chemical Properties

Melting point:

96-98°C

Boiling point:

330.8±27.0 °C(Predicted)

Density 

1.893±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, protect from light

Appearance

Light yellow to yellow Solid

Sensitive 

Light Sensitive

Safety Information

Risk Statements 

23/24/25

Safety Statements 

36/37-45

HS Code 

2909309090

MSDS

• Language:English Provider:ALFA

4-Iodo-2-nitroanisole Usage And Synthesis

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 2427, 1969 DOI: 10.1017/S0009838800024678

Synthesis

General procedure for the synthesis of 4-iodo-2-nitroanisole from 2-nitroanisole: To a stirred solution of 2-nitroanisole (1 mmol) in dichloromethane (CH2Cl2) or 1,2-dichloroethane ((CH2Cl)2) (0.1 M) was added sequentially Ph3PAuNTf2 (0.025 mmol, 19 mg; if using the 2:1 complex of Ph3PAuNTf2 with toluene) and N-iodosuccinimide (NIS, 1.1 mmol, 248 mg). The reaction mixture was stirred at room temperature or reacted under reflux conditions until complete conversion of the feedstock was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the resulting crude product was purified by fast column chromatography using different ratios of hexane and ethyl acetate (EtOAc) as eluents, resulting in pure 4-iodo-2-nitroanisole.

References

[1] Synlett, 2014, vol. 25, # 3, p. 399 - 402
[2] Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3552 - 3555
[3] Tetrahedron, 2004, vol. 60, # 41, p. 9113 - 9119
[4] Synthetic Communications, 2007, vol. 37, # 8, p. 1259 - 1265
[5] Synthesis, 2006, # 7, p. 1195 - 1199

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