Skip to Content
Merck
All Photos(3)

Documents

248835

Sigma-Aldrich

p-Toluenesulfonyl cyanide

technical grade, 95%

Synonym(s):

p-Tolylsulfonyl cyanide, Tosyl cyanide

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
CH3C6H4SO2CN
CAS Number:
19158-51-1
Molecular Weight:
181.21
Beilstein:
2048159
EC Number:
242-849-1
MDL number:
MFCD00009977
UNSPSC Code:
12352100
PubChem Substance ID:
24854953
NACRES:
NA.22

grade

technical grade

Assay

95%

form

solid

bp

105-106 °C/1 mmHg (lit.)

mp

47-50 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C8H7NO2S/c1-7-2-4-8(5-3-7)12(10,11)6-9/h2-5H,1H3

InChI key

JONIMGVUGJVFQD-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

p-Toluenesulfonyl cyanide is an electron-deficient nitrile. It undergoes hetero-Diels-Alder reaction with silyl enol ether of cyclohexenone to yield hydrolytically sensitive [4+2] adduct. It also undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles. p-Toluenesulfonyl cyanide also reacts with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield sulfinates.

Application

p-Toluenesulfonyl cyanide can be used in:
  • The preparation of polyfunctional nitriles.
  • Free-radical cyanation of B-alkylcatecholboranes.
  • The synthesis of 4-hyroxypyridines by hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H312 + H332,H314

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Diethyl malonimidate dihydrochloride

Sigma-Aldrich

406554

Diethyl malonimidate dihydrochloride

A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-acyltetrazoles from azides and acyl cyanides.
Zachary P Demko et al.
Angewandte Chemie (International ed. in English), 41(12), 2113-2116 (2002-06-17)
Synthesis of 2-(Arylsulfonyl)-4-hydroxypyridines by Hetero-Diels-Alder Reaction of 1,3-Bis-Silyl Enol Ethers with Arylsulfonyl Cyanides
Thomas Emmrich, et al.
Synthesis, 2551-2555 (2006)
Radical-mediated alkenylation, alkynylation, methanimination, and cyanation of B-alkylcatecholboranes.
Arnaud-Pierre Schaffner et al.
Angewandte Chemie (International ed. in English), 45(35), 5847-5849 (2006-08-05)
Cynthia K McClure et al.
The Journal of organic chemistry, 68(21), 8256-8257 (2003-10-11)
The hetero-Diels-Alder reaction of an electron-deficient nitrile, p-toluenesulfonyl cyanide, with the silyl enol ether of cyclohexenone produced a hydrolytically sensitive [4 + 2] adduct in good yield. Use of Mander's reagent, ethyl cyanoformate, with the same diene, produced an unstable
O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide.
Barton DHR, et al.
Tetrahedron, 47(44), 9167-9178 (1991)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service