19158-51-1

Basic information

• Product Name: Tosyl cyanide
• Synonyms: p-tolylsulfonylforMonitrile;p-Toluenesulfonyl cyanide technical grade, 95%;Toluene-4-sulphonylcyanide,tech;P-TOLYLSULFONYL CYANIDE;p-toluenesulphonyl cyanide;P-TOLUENESULFONYL CYANIDE;TOSYL CYANIDE;4-Toluenesulfonyl Cyanide
• CAS NO: 19158-51-1
• Molecular Formula: C₈H₇NO₂S
• Molecular Weight: 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
• Article Data: 8

Chemical Properties

• Melting Point: 47-50 °C(lit.)
• Boiling Point: 105-106 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.3055 (rough estimate)
• Vapor Pressure: 0.0125mmHg at 25°C
• Refractive Index: 1.5650 (estimate)
• Storage Temp.: 2-8°C
• BRN: 2048159
• CAS DataBase Reference: Tosyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: Tosyl cyanide(19158-51-1)
• EPA Substance Registry System: Tosyl cyanide(19158-51-1)

Safety Data

• Hazard Codes: C
• 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
• Hazardous Substances Data: 19158-51-1(Hazardous Substances Data)

Usage

Description

Tosyl cyanide, also known as p-Toluenesulfonyl cyanide, is an electron-deficient nitrile that exists as a white powder. It is known for its reactivity in various chemical reactions, such as hetero-Diels-Alder reactions and free-radical cyanations.

Uses

Used in Chemical Synthesis:
Tosyl cyanide is used as a reagent in the preparation of polyfunctional nitriles, which are essential building blocks in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
Tosyl cyanide is used as a reagent in the free-radical cyanation of B-alkylcatecholboranes, a process that is crucial in the development of new pharmaceutical compounds.
Used in Organic Chemistry:
Tosyl cyanide is used as a component in a hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers, leading to the synthesis of 4-hydroxypyridines, which are important intermediates in the synthesis of various pharmaceuticals and agrochemicals.
Used in Synthesis of 5-Sulfonyl Tetrazoles:
Tosyl cyanide undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles, which are valuable compounds in the field of organic chemistry and material science.
Used in Synthesis of Sulfinate Esters:
Tosyl cyanide 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, which are useful intermediates in organic synthesis and have applications in the pharmaceutical and agrochemical industries.

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 3351, 1969 DOI: 10.1017/S0009838800024678

InChI:InChI=1/C9H14N2/c1-11(2)9-5-3-8(7-10)4-6-9/h3-6H,7,10H2,1-2H3

Upstream product

• 824-79-3 sodium 4-methylbenzenesulfinate 
• 506-77-4 cyanogen chloride 
• 5285-74-5 4-tolyl thiocyanate 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 142272-77-3 1,9-Dimethyl-3-(toluene-4-sulfonyl)-9H-β-carboline 
• 133523-50-9 4-methyl-3-(p-toluenesulfonyl)-1,2,4-thiadiazoline-5-thione 
• 135802-73-2 4-Methyl-benzenesulfinic acid octadecyl ester 
• 112033-26-8 trans-2-methyl-5-(1-cyano-1-methylethyl)-3-(p-tolylsulphonyl)cyclohexene 
• 24865-83-6 4-methyl-N-(1-phenylethylidene)benzenesulfonamide 
• 143121-72-6 (E)-2-<<('4-methylphenyl)sulfonyl>imino>-4-phenyl-3-butene 
• 49805-27-8 3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene 
• 112033-27-9 trans-3-cyano-5-(p-tolylsulphonyl)-1-cyclopentene 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 2621-78-5 ethyl N-benzylcarbamate 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 79378-71-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-p-toluenesulfinate 
• 1003-31-2 thiophene-2-carbonitrile 
• 1527-89-5 3-methoxybenzonitrile 

Related news

A novel sulfinylation of alkenes by Tosyl cyanide (cas 19158-51-1) with titanium(IV) chloride07/25/2019

Tosyl cyanide is activated by titanium(IV) chloride to generate a tolylsulfinyl chloride equivalent, which readily stereo- and regio-specifically adds to certain alkenes to provide β-chlorosulfoxides. These chlorides rapidly hydrolyse on silica gel to provide β-hydroxysulfoxides in stereocontr...detailed

Relevant articles and documents

P-Anisaldehyde-Photosensitized Sulfonylcyanation of Chiral Cyclobutenes: Enantioselective Access to Cyclic and Acyclic Systems Bearing All-Carbon Quaternary Stereocenters

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