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248835

Sigma-Aldrich

p-Toluenesulfonyl cyanide

technical grade, 95%

Synonym(s):

p-Tolylsulfonyl cyanide, Tosyl cyanide

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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

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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)

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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)
Preparation of polyfunctional nitriles by the cyanation of functionalized organozinc halides with p-toluenesulfonyl cyanide.
Klement I, et al.
Tetrahedron Letters, 34(29), 4623-4626 (1993)
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
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