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733423

Sigma-Aldrich

N,N-Dichloro-p-toluenesulfonamide

97%

Synonym(s):

Dichloramine T

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About This Item

Empirical Formula (Hill Notation):
C7H7Cl2NO2S
CAS Number:
473-34-7
Molecular Weight:
240.11
EC Number:
207-462-4
MDL number:
MFCD00058929
UNSPSC Code:
12352002
PubChem Substance ID:
329764814
NACRES:
NA.22

assay

97%

reaction suitability

reagent type: oxidant

mp

79-83 °C

storage temp.

−20°C

SMILES string

Cc1ccc(cc1)S(=O)(=O)N(Cl)Cl

InChI

1S/C7H7Cl2NO2S/c1-6-2-4-7(5-3-6)13(11,12)10(8)9/h2-5H,1H3

InChI key

ARGDYOIRHYLIMT-UHFFFAOYSA-N

Application

N,N-Dichloro-p-toluenesulfonamide (TsNCl2) can be used as:        
  • A nitrogen source for the preparation of aziridines from electron-deficient α,β-unsaturated alkenes in the presence of palladium catalyst.      
  • A reagent in the synthesis of dichlorohaloamines by aminohalogenation of functionalized olefins using copper(I) chloride or 4-dimethylaminopyridine (DMAP) catalyst.       
  • A chlorinating agent in the regioselective synthesis of α-mono chlorosulfoxides from dialkyl sulfoxides or alkyl aryl sulfoxides.

pictograms

Flame over circleExclamation mark
GHS03,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Ox. Sol. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

5.1A - Strongly oxidizing hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Palladium-catalyzed aziridination of alkenes using N, N-dichloro-p-toluenesulfonamide as nitrogen source
Han J, et al.
Tetrahedron Letters, 47(40), 7225-7228 (2006)
T Jyotsna et al.
International journal of radiation applications and instrumentation. Part B, Nuclear medicine and biology, 13(5), 549-550 (1986-01-01)
Iodination of insulin using N-dichloro-p-toluene sulphonamide(dichloramine-T) has been standardised. Dichloramine-T, a water insoluble derivative of chloramine-T showed excellent properties as an iodination reagent, for the preparation of radiolabeled insulin for use in radioimmunoassay. Iodination using dichloramine-T could be done at
Facile Synthesis of α-Chlorosulfoxide Using the N, N?-Dichloro-p-toluenesulfonamide
Kim YH, et al.
Chemistry Letters (Jpn), 19(1), 79-82 (1990)
Catalytic aminohalogenation reaction of β-nitrostyrenes with N, N-dichloro-p-toluenesulfonamide resulting in dichlorinated haloamides with opposite regiochemistry to previous systems
Zhi S, et al.
Synthesis, 2008(10), 1570-1574 (2008)
S M Moerlein et al.
International journal of radiation applications and instrumentation. Part A, Applied radiation and isotopes, 38(2), 85-90 (1987-01-01)
A series of metallated arenes bearing sigma-bonded tin, mercury, germanium, boron, or silicon were evaluated as labeling substrates for the generator-produced positron emitter 122I(t1/2 = 3.6 min). Using dichloramine-T with 122I, radiochemical yields exceeding 90% were achieved after 1 min
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