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

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

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 
• 98-59-9 p-toluenesulfonyl chloride 
• 5285-74-5 4-tolyl thiocyanate 

Downstream Products

• 51915-25-4 C₉H₁₀ClNO₂S₂ 
• 51915-23-2 C₁₆H₁₄Cl₂N₂O₄S₃ 
• 27545-58-0 3-phenyl-5-(toluene-4-sulfonyl)-[1,2,4]oxadiazole 
• 52894-17-4 C₁₄H₁₇Cl₂NO₂S₂ 
• 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 
• 35274-27-2 2-(p-tolylsulphonylmethyl)hexanenitrile 
• 112033-21-3 2-Butyl-4-(toluene-4-sulfonylmethyl)-octanenitrile 
• 112033-24-6 exo-2-cyano-exo-6-(p-tolylsulphonyl)bicyclo<3.3.0>octane 
• 112033-25-7 1-(p-tolylsulphonylmethyl)-4-(1-cyano-1-methylethyl)-1-cyclohexene 
• 135802-73-2 4-Methyl-benzenesulfinic acid octadecyl ester 
• 263-06-9 6H,12H-Dibenzo<1,5>dithiocin 
• 135216-84-1 2-(4-Methylphenylsulfonyl)-4H-1,3-benzothiazine 
• 69380-84-3 N-isopropylidene-4-methylbenzensulfonamide 

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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

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