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402869

Sigma-Aldrich

Chloramine T trihydrate

ACS reagent, 98%

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

grade

ACS reagent

Quality Level

Assay

98%
98.0-103.0% (ACS specification)

form

powder

reaction suitability

reagent type: oxidant

impurities

<1.5% insolubles (alcohol)

pH

8.0-10.0 (25 °C, 5%)

mp

167-170 °C (lit.)

solubility

H2O: passes test

suitability

passes test for determination of bromide

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 (CAT) trihydrate is a commonly used reagent for organic synthesis especially in heterocyclic chemistry. CAT is an active chlorine compound that shows antimicrobial activity.

Application

Chloramine T trihydrate may be used as an oxidizing agent in the synthesis of 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine derivatives and novel isoxazolines.
It may also be used in the synthesis of the following compounds:
  • Nitrile imines by the oxidative dehydrogenation of N-(nitrobenzyl)-imidazole aldehyde hydrazine.
  • Mono-N-tosylated-1,2-diamines.
  • 3,5-Disubstituted isoxazoles.
  • Fused 3,6-disubstituted triazolothiadiazoles by the oxidative cyclization of N-heteroaryl-substituted hydrazones.
Nitrene source for aziridinations and aminohydroxylations.

Packaging

Capable of oxidative cyclization to produce various heterocycles.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Supplementary Hazards

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

377.6 °F - closed cup

Flash Point(C)

192 °C - closed cup


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Facile Synthesis of 3, 6-Disubstituted-1, 2, 4-triazolo-[3, 4-b]-1, 3, 4-thiadiazoles via Oxidative Cyclization of N-Heteroaryl-Substituted Hydrazones and Their Biological Activity.
Himaja M, et al.
Journal of Heterocyclic Chemistry, 49(4), 823-828 (2012)
Novel (+)-3-Carene Derivatives and Their Application in Asymmetric Synthesis.
Roszkowski P, et al.
Synthesis, 47(04), 569-574 (2015)
Mogilaiah, K.; Reddy, G. R.
J. Chem. Res. (M), 145-145 (2004)
Rudolph, J. et al
Angewandte Chemie (International Edition in English), 35, 2810-2810 (1996)
Silica-water reaction media: its application to the formation and ring opening of aziridines.
Satoshi Minakata et al.
Angewandte Chemie (International ed. in English), 43(1), 79-81 (2003-12-25)

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