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Synlett 2005(18): 2857-2858  
DOI: 10.1055/s-2005-918936
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Chloramine-T (Sodium N-Chloro-p-toluenesulfonamide)

Geetanjali Agnihotri*
Medicinal and Process Chemistry Division, Central Drug Research Institute, Chattar Manzil Palace, Lucknow 226001, UP, India.
e-Mail: geetagni@yahoo.co.in;
Further Information

Publication History

Publication Date:
12 October 2005 (online)

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Introduction

Sodium N-chloro-p-toluenesulfonamide, commonly known as Chloramine-T, has diverse chemical properties. Several other N-halogeno-N-metalloarylsulfonamides are also available, such as Chloramine B, Bromamine T, Bromamine B, and Iodamine-T. Chloramine-T in the hydrate form has been used in various types of chemical reactions more extensively than others in this group. It is commercially available, inexpensive, water-tolerant, non-toxic, easy to handle, and can be used without further purification. The usefulness of Chloramine-T is that it behaves as a source of both ‘halonium’ ion as well as a ‘nitrogen ­anion’. As a result, these reagents react with a surprising range of functional groups, leading to an array of mole­cular transformations. The synthetic applications of Chloramine-T have been well-documented for amino­hydroxylation, aminochalcogenation of alkenes, allylic aminations, and aziridinations.