NITROMETHYL PHENYL SULFONE Chemical Properties

Melting point:

78-80 °C

Boiling point:

122-123 °C

Density 

1.397±0.06 g/cm3(Predicted)

solubility 

insoluble in water; soluble in CH2Cl2, hot alcohol.

pka

4.07±0.29(Predicted)

form 

crystals

BRN 

1876502

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22

Safety Statements 

22-24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2930909899

MSDS

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NITROMETHYL PHENYL SULFONE Usage And Synthesis

Uses

Phenylsulfonylnitromethane is a precursor for α-nitro sulfones and a precursor for phenylsulfonylnitrile oxide for 1,3-dipolar cycloadditions.

Synthesis

The Preparative Method of Phenylsulfonylnitromethane: Nitromethane, Sodium Benzenesulfonate, and Iodine have been added sequentially to a cold (0-5 °C) DMF solution of Sodium Methoxide. The reagent can be converted to NaO2N=CHSO2Ph (1) and LiO2N=CHSO2Ph (2) using NaOMe and LiOMe, respectively.

Purification Methods

Recrystallise the sulfone from CHCl3, or 95% EtOH, then sublime it at 100-120o/0.1 Torr and recrystallise again. It is an acidic analogue of nitromethane used for the general synthesis of aliphatic acids and nitriles and in cycloaddition reactions with olefins to form heterocycles. [Wade et al. J Org Chem 46 765 1981, 49 4595 1984, Beilstein 6 II 292.]

Precautions

Indefinitely stable; the nitronate salts (1) and (2) can be stored dry without decomposition for several weeks but, like all nitronate salts, they are explosive: (2) vigorously decomposes above 150 °C

NITROMETHYL PHENYL SULFONE(21272-85-5)Related Product Information

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