Ammonia-free synthesis of 3-trifluoromethyl-3-phenyldiaziridine

ABSTRACT

An ammonia-free synthesis of 3-trifluoromethyl-3-phenyldiaziridine, an important intermediate in the synthesis of a widely used photolabel 3-trifluoromethyl-3-phenyldiazirine, is described. By avoiding the use of volatile, corrosive, and toxic anhydrous ammonia, the major hazard involved in the synthesis of this widely used photolabel is eliminated. Furthermore, this synthesis is convenient compared to the conventional route, since it is significantly less time consuming and, due to the absence of liquid ammonia, this method does not require the maintenance of low temperature for prolonged periods.

GRAPHICAL ABSTRACT

KEYWORDS:

• Diaziridine
• diazirine
• o-mesitylenesulfonyl hydroxylamine
• photoaffinity label
• photolabel

Additional information

Funding

This Work was supported by the National Institute of General Medical Sciences [Grant Number R01GM097118].