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248835

Sigma-Aldrich

p-Toluenesulfonyl cyanide

technical grade, 95%

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Synonym(s):
p-Tolylsulfonyl cyanide, Tosyl cyanide
Linear Formula:
CH3C6H4SO2CN
CAS Number:
Molecular Weight:
181.21
Beilstein/REAXYS Number:
2048159
EC Number:
MDL number:
PubChem Substance ID:
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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1 of 4

This Item
189278T35955188204
vibrant-m

248835

p-Toluenesulfonyl cyanide

vibrant-m

189278

p-Toluenesulfonyl isocyanate

vibrant-m

T35955

p-Toluenesulfonyl chloride

vibrant-m

188204

p-Toluenesulfonylmethyl isocyanide

assay

95%

assay

96%

assay

≥98%

assay

98%

bp

105-106 °C/1 mmHg (lit.)

bp

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

bp

134 °C/10 mmHg (lit.)

bp

-

mp

47-50 °C (lit.)

mp

-

mp

65-69 °C (lit.)

mp

109-113 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

2-8°C

form

solid

form

liquid

form

-

form

solid

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

signalword

Danger

Hazard Classifications

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

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Customers Also Viewed

Slide 1 of 4

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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)
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)
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)
O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide.
Barton DHR, et al.
Tetrahedron, 47(44), 9167-9178 (1991)
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)

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