O-Mesitylenesulfonylhydroxylamine Chemical Properties

Melting point:

93-94 °C

Boiling point:

350.6±52.0 °C(Predicted)

Density 

1.240

storage temp. 

Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

very soluble in diethyl ether, chloroform, dichloromethane, benzene, ethanol, THF; insoluble in water and petroleum ether

form 

Oil

pka

-4.59±0.70(Predicted)

color 

Pale Yellow to Pale Beige

Stability:

Do not dry. Will explode. Explosive.

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2930909899

O-Mesitylenesulfonylhydroxylamine Usage And Synthesis

Uses

O-Mesitylenesulfonylhydroxylamine is an oxidizing and aminating reagent with great potential to oxidatively eliminate the cysteine thiol modification to dehydroalanine.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1239, 1973 DOI: 10.1021/jo00946a045
Synthesis, p. 788, 1975 DOI: 10.1055/s-1975-23927

Synthesis

To a solution of 89 g (330 mmol) O-(mesitylsulfonyl)acetohydroxamate (1) in dioxane is added with stirring 30 mL perchloric acid (70%) at 0 °C within 10 min, and then stirred for another 10 min. After adding about 20 mL of the acid, the reaction mixture becomes pasty. The crude reaction mixture is poured into ice water to give a white solid of O-(mesitylsulfonyl)hydroxylamine, which is collected, washed with cold water (500 mL), then with cold petroleum ether (300 mL), and dried by maintaining suction for about 1 h; yield 55-65 g (77-92%).
The product should be stored in a refrigerator below 0 °C. Iodometric titration indicates that O-Mesitylenesulfonylhydroxylamine, thus prepared, contains 20-30% water. It can be used for most applications. Further purification can be achieved by the dissolution of a small amount of diethyl ether at room temperature and precipitation with petroleum ether.

Precautions

O-(mesitylsulfonyl)hydroxylamine must be handled with care. The first report about a rapid decomposition when standing at room temperature appeared in 1977. After an explosion of O-Mesitylenesulfonylhydroxylamine during storage below 0 °C, as suggested above, it is strongly recommended that O-Mesitylenesulfonylhydroxylamine be prepared immediately before use and not stored.

O-Mesitylenesulfonylhydroxylamine(36016-40-7)Related Product Information

• 1,2,4-Trimethylbenzene
• Mesitylene
• N-Acetylsulfanilyl chloride
• Dimethyl sulfone
• 1,3,5-Trimethoxybenzene
• Sulfanilamide
• Phthalic anhydride
• 6-Hydroxypurine
• Mesitylene-2-sulfonyl chloride
• L-ACYLASE
• tert-Butyl (Mesitylsulfonyl)oxycarbaMate
• Ethyl O-mesitylsulfonylacetohydroxamate
• HYDROXYLAMINE
• ACETOXIME O-(2,4,6-TRIMETHYLPHENYLSULFONATE)
• O-Mesitylenesulfonylhydroxylamine