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Sigma-Aldrich

Chloramine T trihydrate

reag. Ph. Eur., 98.0-103.0%

Synonym(s):

N-Chloro-p-toluenesulfonamide sodium salt

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About This Item

Linear Formula:
CH3C6H4SO2NClNa · 3H2O
CAS Number:
Molecular Weight:
281.69
Beilstein:
3924168
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

Agency

USP/NF
reag. Ph. Eur.

Quality Level

Assay

98.0-103.0%

impurities

≤1.5% insoluble in ethanol

pH

8-10 (20 °C, 5%)

mp

167-170 °C (lit.)

SMILES string

O.O.O.Cc1ccc(cc1)S(=O)(=O)N([Na])Cl

InChI

1S/C7H7ClNO2S.Na.3H2O/c1-6-2-4-7(5-3-6)12(10,11)9-8;;;;/h2-5H,1H3;;3*1H2/q-1;+1;;;

InChI key

NZYOAGBNMCVQIV-UHFFFAOYSA-N

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General description

Chloramine-T trihydrate is a widely used oxidizing agent in organic synthesis. It acts as a source of halonium cation and nitrogen anion and thus acts as a base and nucleophile. Due to its reactivity with a wide range of functional groups, it is involved in different molecular transformations. It is effective in acidic, neutral, and basic conditions.

Application

Chloramine-T trihydrate can be used as:
  • A reagent for chlorination in drinking water treatment.
  • A dehydrogenating agent for the oxidative dehydrogenation of aromatic aldehyde phenylhydrazones to synthesize nitrile imines.
  • The nitrene source for the aziridination of alkenes and the amidation of cyclic ethers.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B

Supplementary Hazards

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Nitrene transfer reactions catalysed by copper (I) complexes in ionic liquid using chloramine-T
Cano I, et al.
Dalton Transactions (2007)
Crystal and molecular structure of chloramine-T trihydrate. Absence of a sodium-nitrogen interaction in the oxidant. N-chloro-N-sodiotoluene-p-sulfonamide.
Olmstead MM and Power PP.
Inorganic Chemistry, 25(22), 4057-4058 (1986)
Synthesis of 3, 4-diaryl-1-phenyl-4, 5-dihydro-1H-pyrazole-5-carbonitriles via 1, 3-dipolar cycloaddition reactions
Prabhashankar J, et al.
Turkish Journal of Chemistry, 37, 853-857 (2013)
Chloramine-T (N-chloro-p-toluenesulfonamide sodium salt), a versatile reagent in organic synthesis and analytical chemistry: An up to date review
Nayak Y, et al.
Journal of Saudi Chemical Society, 101416-101416 (2022)
Chloramine T and related N-halogeno-N-metallo reagents.
Campbell MM and Johnson G.
Chemical Reviews, 78(1), 65-87 (1978)

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