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Sigma-Aldrich

p-Toluenesulfonyl isocyanate

96%

Synonym(s):

Tosyl isocyanate

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About This Item

Linear Formula:
CH3C6H4SO2NCO
CAS Number:
4083-64-1
Molecular Weight:
197.21
Beilstein/REAXYS Number:
391287
EC Number:
223-810-8
MDL number:
MFCD00002030
UNSPSC Code:
12352100
PubChem Substance ID:
24851374
NACRES:
NA.22

vapor pressure

1 mmHg ( 100 °C)

Quality Level

200

assay

96%

form

liquid

refractive index

n20/D 1.534 (lit.)

bp

144 °C/10 mmHg (lit.)
275-278 °C (lit.)

density

1.291 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C8H7NO3S/c1-7-2-4-8(5-3-7)13(11,12)9-6-10/h2-5H,1H3

InChI key

VLJQDHDVZJXNQL-UHFFFAOYSA-N

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General description

p-Toluenesulfonyl isocyanate undergoes palladium-catalyzed bis-allylation reaction with allylstannanes and allyl chlorides.

Application

p-Toluenesulfonyl isocyanate has been used as :
  • derivatization reagent in determination of 3-α-hydroxy tibolone in human plasma by LC-MS/MS
  • derivatization reagent in simultaneous quantitative analysis of diethylene glycol and propylene glycol in pharmaceutical products by HPLC
  • as reagent in the preparation of acetylated syn-1,2-diols, oxazolidin-2-ones, 2,3-diamino acids and N-tosylcarbonamides

pictograms

Exclamation markHealth hazard
GHS07,GHS08

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

294.8 °F - closed cup

flash_point_c

146 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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N Solin et al.
Organic letters, 3(6), 909-912 (2001-03-27)
A tandem bis-allylation of p-toluenesulfonyl isocyanate can be achieved by palladium-catalyzed three-component coupling reaction with allylstannanes and allyl chlorides. A high level of regioselectivity can be obtained by the appropriate choice of the allylic substituents. The reaction mechanism and the
Fabiana Fernandes de Santana e Silva Cardoso et al.
Biomedical chromatography : BMC, 27(11), 1457-1462 (2013-07-03)
A new method was developed for the quantitation of 3-α-hydroxy tibolone, in human plasma, after oral administration of a tablet formulation containing tibolone (2.5 mg). 3-α-Hydroxy tibolone was extracted by a liquid-liquid procedure, using cyproterone acetate as internal standard and chlorobutane
Tetrahedron Letters, 34, 951-951 (1993)
Tetrahedron, 47, 2263-2263 (1991)
Tetrahedron Letters, 34, 1867-1867 (1993)
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