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Tosyl cyanide

Tosyl cyanide Basic information
Product Name:Tosyl cyanide
Synonyms:p-tolylsulfonylforMonitrile;p-Tosyl cyanide;Toluene-4-sulfonyl cyanide 98%;p-Toluenesulfonyl cyanide technical grade, 95%;Toluene-4-sulphonylcyanide,tech;P-TOLYLSULFONYL CYANIDE;p-toluenesulphonyl cyanide;P-TOLUENESULFONYL CYANIDE
CAS:19158-51-1
MF:C8H7NO2S
MW:181.21
EINECS:242-849-1
Product Categories:Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
Mol File:19158-51-1.mol
Tosyl cyanide Structure
Tosyl cyanide Chemical Properties
Melting point 47-50 °C (lit.)
Boiling point 105-106 °C/1 mmHg (lit.)
density 1.3055 (rough estimate)
refractive index 1.5650 (estimate)
Fp >230 °F
storage temp. 2-8°C
solubility Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate
form crystalline solid
color White
BRN 2048159
Stability:Hygroscopic, Moisture Sensitive
CAS DataBase Reference19158-51-1(CAS DataBase Reference)
Safety Information
Hazard Codes C
Risk Statements 20/21-34
Safety Statements 26-27-28-36/37/39-45
RIDADR UN 3261 8/PG 2
WGK Germany 3
F 10-21
HazardClass 8
PackingGroup III
HS Code 2930909899
MSDS Information
ProviderLanguage
SigmaAldrich English
Tosyl cyanide Usage And Synthesis
Chemical PropertiesWhite powder
Usesp-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.
UsesTosyl 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 Descriptionp-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.
Tosyl cyanide Preparation Products And Raw materials
Preparation Products2-Azabicyclo[2.2.1]hept-5-en-3-one-->Methyl 3-cyano-4-Methylbenzoate-->tert-butyl 3-cyanomorpholine-4-carboxylate-->5-KETOHEXANENITRILE-->2-FUROYLACETONITRILE-->2-Bromothiophene-3-carbonitrile-->3-BROMOTHIOPHENE-2-CARBONITRILE-->1-Adamantanecarbonitrile-->4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile-->(1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE-->4-CYANOCYCLOHEXANONE CYCLIC ETHYLENE ACETAL-->1-N-Boc-3-Cyanopyrrolidine-->2-Cyanothiazole-->4-Hydroxy-3-methoxybenzonitrile-->Cyanoacetylene-->Ethyl 2-cyano-3-hydroxybut-2-enoate-->Ethyl 4-(4-methylphenyl)sulfanylbutanoate
p-Toluenesulfonamide Copper(I) Cyanide Chloral hydrate tosyl cyanide S (R)-(+)-Methyl p-tolyl sulfoxide Toluene (S)-(-)-METHYL P-TOLYL SULFOXIDE TOLBUTAMIDE 1-Methyl-4-(methylsulfonyl)-benzene 4-Methylbenzenesulfonhydrazide 1-METHYL-4-(METHYLSULFINYL)BENZENE (4-Methylthio)toluene HYDROGEN CYANIDE sodium cyanide Methyl thiocyanate Cyanide Tosyl cyanide METHYL PHENYL SULFOXIDE
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