O-Mesitylenesulfonylhydroxylamine

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H315：피부에 자극을 일으킴

  H319：눈에 심한 자극을 일으킴

  H335：호흡 자극성을 일으킬 수 있음

• 예방조치문구

  P280：보호장갑/보호의/보안경/안면보호구를 착용하시오.

  P301+P312：삼켜서 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.

O-Mesitylenesulfonylhydroxylamine 화학적 특성, 용도, 생산

• 용도

  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.

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