248835
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:
Molecular Weight:
181.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
242-849-1
Beilstein/REAXYS Number:
2048159
MDL number:
Assay:
95%
Form:
solid
grade
technical grade
Quality Level
assay
95%
form
solid
bp
105-106 °C/1 mmHg (lit.)
mp
47-50 °C (lit.)
functional group
sulfone, thiocyanate
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
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
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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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 248835-1G | 04061825928371 |
| 248835-5G | 04061825928388 |