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)

Flash point:

>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 Reference

19158-51-1(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

• Language:English Provider:SigmaAldrich

Tosyl cyanide Usage And Synthesis

Chemical Properties

White powder

Uses

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.

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.

Tosyl cyanide(19158-51-1)Related Product Information

• Chloral hydrate
• TOLBUTAMIDE
• 4-Methylbenzenesulfonhydrazide
• p-Toluenesulfonamide
• Copper(I) Cyanide
• Tosyl chloride
• Tosyl azide
• P-Toluenesulfonic anhydride
• p-Toluenesulfonic acid monohydrate
• Ethyl p-toluenesulfonate
• Methyl p-toluenesulfonate
• P-TOLUENESULFONIC ACID N-BUTYL ESTER
• HYDROGEN CYANIDE
• (4-Methylthio)toluene
• METHYL PHENYL SULFOXIDE
• 1-METHYL-4-(METHYLSULFINYL)BENZENE
• Toluene
• Methyl thiocyanate