Bromamine-T (TsNBrNa): A Biologically Significant, Versatile Bromo-Organic Reagent

Sauvik Kashyap; Prodeep Phukan

doi:10.1055/a-2089-4821

Synlett, Table of Contents

Synlett 2024; 35(07): 753-776
DOI: 10.1055/a-2089-4821

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Bromamine-T (TsNBrNa): A Biologically Significant, Versatile Bromo-Organic Reagent

Sauvik Kashyap

,

Prodeep Phukan ∗

Abstract

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Abstract

Bromamine-T (BAT) is a notable member of a special class of compounds called organic haloamines, which are oxidising agents. It can act as the source of halonium ions, hypohalite species, and N-anions, whilst also displaying basic and nucleophilic properties. Bromamine-T finds wide application as an efficient reagent for various organic transformations, such as aminobromination, amination, oxidation, and others. It can be used under mild conditions and has low toxicity. Moreover, due to its immense biological significance, this reagent is piquing the interest of many researchers.

1 Introduction

1.1 The Sodium Salt of N-Bromo-p-toluenesulfonamide (Bromamine-T or TsNBrNa): Reagent Overview

1.2 Physical Properties of Bromamine-T

1.3 Preparation and Characterisation of Bromamine-T

2 Biological Significance of Bromamine-T

3 Organic Transformations Using Bromamine-T

3.1 Aminobromination

3.2 Amination

3.3 Aminohydroxylation

3.4 Aziridination

3.5 Bromination

3.6 Oxidation: Kinetic and Mechanistic Studies

4 Conclusion

Key words

bromamine-T - halonium ions - hypohalite - aminobromination - amination - oxidation

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References

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