| Identification | More | [Name]
Tosyl cyanide | [CAS]
19158-51-1 | [Synonyms]
P-TOLUENESULFONYL CYANIDE
p-toluenesulphonyl cyanide
P-TOLYLSULFONYL CYANIDE
TOSYL CYANIDE
4-Toluenesulfonyl Cyanide
P-TOLUENESULFONYL CYANIDE, TECH., APPROX . 95%
4-TolueenesulfonylCyanide
P-TOLUENE SULFONYL CYANIDE(P-TOLYLSULFNYL CYANIDE)
4-TOLUENESULFONYLCYANIDE, 95+%
toluene-4-sulfonyl cyanide
p-Tolylsulfonyl cyanide, Tosyl cyanide | [EINECS(EC#)]
242-849-1 | [Molecular Formula]
C8H7NO2S | [MDL Number]
MFCD00009977 | [Molecular Weight]
181.21 | [MOL File]
19158-51-1.mol |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R20/21:Harmful by inhalation and in contact with skin .
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [F ]
10-21 | [HazardClass ]
8 | [PackingGroup ]
III |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
Tosyl cyanide is used in a free-radical cyanation of B-alkylcatecholboranes. Also used as a component in a hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers leading to 4-hyroxypyridines.
| [Synthesis Reference(s)]
Tetrahedron Letters, 10, p. 3351, 1969 DOI: 10.1017/S0009838800024678 | [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. |
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