248835

p-Toluenesulfonyl cyanide

technical grade, 95%

• Synonym(s): p-Tolylsulfonyl cyanide, Tosyl cyanide
• Linear Formula: CH₃C₆H₄SO₂CN
• CAS Number: 19158-51-1
• Molecular Weight: 181.21
• Beilstein/REAXYS Number: 2048159
• EC Number: 242-849-1
• MDL number: MFCD00009977
• UNSPSC Code: 12352100
• PubChem Substance ID: 24854953
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H312 + H332,H314
• pcodes: P260 - P271 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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