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Sigma-Aldrich

p-Toluenesulfonyl isocyanate

96%

Synonym(s):

Tosyl isocyanate

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25 G
$44.40
100 G
$46.70
500 G
$137.00

About This Item

Linear Formula:
CH3C6H4SO2NCO
CAS Number:
Molecular Weight:
197.21
Beilstein/REAXYS Number:
391287
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
assay:
96%

$44.40


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vapor pressure

1 mmHg ( 100 °C)

Quality Level

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[1].

Application

p-Toluenesulfonyl isocyanate has been used as :
  • derivatization reagent in determination of 3-α-hydroxy tibolone in human plasma by LC-MS/MS[2]
  • derivatization reagent in simultaneous quantitative analysis of diethylene glycol and propylene glycol in pharmaceutical products by HPLC[3]
  • as reagent in the preparation of acetylated syn-1,2-diols[4], oxazolidin-2-ones[5], 2,3-diamino acids[6] and N-tosylcarbonamides[7]

pictograms

Health hazardExclamation mark

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


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Tetrahedron Letters, 34, 1867-1867 (1993)
Tetrahedron Letters, 34, 951-951 (1993)
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
Tetrahedron, 47, 2263-2263 (1991)
Inga Mädge et al.
Food chemistry, 187, 491-498 (2015-05-16)
A general contamination of tea with pyrrolizidine alkaloids (PA) has just become known. Here, we report the application and modification of a new HPLC-ESI-MS/MS sum parameter method to quantitate PA content of herbal teas intended for infants, pregnant and lactating

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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