chloramine T

Also known as Chloramine-t, Tolamine, Tochlorine, Tampules, Sodium tosylchloramide, Sodium p-toluenesulfonylchloramide, Sodium p-toluenesulfonchloramide, Sodium chloramine T

Chloramine-T is the organic compound with the formula CH3C6H4SO2NClNa. Both the anhydrous salt and its trihydrate are known. Both are white powders. Chloramine-T is used as a reagent in organic synthesis. It is commonly used as cyclizing agent in the synthesis of aziridine, oxadiazole, isoxazole and pyrazoles. It's inexpensive, has low toxicity and acts as a oxidizing agent. In addition, it also acts as a source of nitrogen anions and electrophilic cations. It may undergo degradation on long term exposure to atmosphere such that care must be taken during its storage.

Chemical data

Formula: C7H7ClNNaO2S
Molecular weight: 227.64 g/mol
IUPAC name: sodium chloro-(4-methylphenyl)sulfonylazanide
SMILES: CC1=CC=C(C=C1)S(=O)(=O)[N-]Cl.[Na+]
InChIKey: VDQQXEISLMTGAB-UHFFFAOYSA-N
Polar surface area: 43.5 Å²
H-bond donors: 0
H-bond acceptors: 3
Formal charge: 0

via PubChem

~3 min read

Encyclopedic overview

9 sections

Contents

Reactions
Uses
Reagent in amidohydroxylation
Oxidant
Disinfectant
Safety
Certifications
References
External links

==Reactions== Chloramine-T contains active (electrophilic) chlorine. Its reactivity is similar to that of sodium hypochlorite. Aqueous solutions of chloramine-T are slightly basic (pH typically 8.5). The pKa of the closely related N-chlorophenylsulfonamide C6H5SO2NClH is 9.5.

Excerpted from Wikipedia’s “chloramine T” article, available under the CC BY-SA 4.0 licence.