Tosyl cyanide

Base Information

• Chemical Name: Tosyl cyanide
• CAS No.: 19158-51-1
• Molecular Formula: C8H7NO2S
• Molecular Weight: 181.215
• Hs Code.: 2926909090
• European Community (EC) Number: 242-849-1
• DSSTox Substance ID: DTXSID50172685
• Nikkaji Number: J224.867K
• Wikidata: Q72509421
• Mol file: 19158-51-1.mol

Synonyms:Tosyl cyanide;19158-51-1;p-Toluenesulfonyl cyanide;4-Methylbenzenesulfonyl cyanide;(4-methylphenyl)sulfonylformonitrile;p-toluene sulfonyl cyanide;p-Toluenesulphonyl cyanide;p-Tolylsulfonyl cyanide;Benzenesulfonyl cyanide, 4-methyl-;4-toluenesulfonyl cyanide;4-methylbenzene-1-sulfonyl cyanide;EINECS 242-849-1;4-tolylsulfonylcyanide;tosyl cyanide;TosCN;TsCN;p-toluensulfonylcyanide;p-tolylsulfonylformonitrile;p-toluene-sulfonyl cyanide;para-toluenesulfonyl cyanide;4-Methylbenzenesulfonylcyanide;SCHEMBL118977;4-TOLUENESULFONYLCYANIDE;AMY323;DTXSID50172685;4-Methylbenzenesulfonyl cyanide #;MFCD00009977;AKOS009156842;CS-W017154;GS-6407;FT-0637802;EN300-49731;H10452;p-Toluenesulfonyl cyanide, technical grade, 95%;A936598;J-012384;F0001-0688

Chemical Property of Tosyl cyanide

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.0125mmHg at 25°C
• Melting Point: 47-50 °C
• Refractive Index: 1.579
• Boiling Point: 289.829 °C at 760 mmHg
• Flash Point: 125.495 °C
• PSA: 66.31000
• Density: 1.286 g/cm³
• LogP: 2.33058
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 181.01974964
• Heavy Atom Count: 12
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

TosylCyanide(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 20/21-34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)C#N
• 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. 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.

Technology Process of Tosyl cyanide

There total 5 articles about Tosyl cyanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.8%

sodium 4-methylbenzenesulfinate (824-79-3) → P-toluenesulfonyl cyanide (19158-51-1)

Guidance literature:

Reference yield: 93.8%

→ P-toluenesulfonyl cyanide (19158-51-1)

Guidance literature:

Reference yield: 90.0%

sodium 4-methylbenzenesulfinate (824-79-3) + cyanogen chloride (506-77-4) → P-toluenesulfonyl cyanide (19158-51-1)

Guidance literature:

With sodium hydroxide; In tetrachloromethane; water;

upstream raw materials:

sodium 4-methylbenzenesulfinate

cyanogen chloride

p-toluenesulfonyl chloride

4-tolyl thiocyanate

Downstream raw materials:

1-phenyl-4-(toluene-4-sulfonyl)-1H-pyrazolo[3,4-d]pyrimidine

(3R,8aR)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridine-5,5-dicarbonitrile

di(4-methyl)phenylthiosulfonate

2-Ethylthio-5-methyl-3-phenyl-6-tosyl-4(3H)-pyrimidinon

Refernces

• 1、 Rao, Weidong,Wang, Fei,Wang, Shun-Yi. "Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides". . p. 8970 - 8979. Retrieved 2021/07/19.
• 2、 Li, Zheng,Xu, Jun. "Solvent-free synthesis of arylsulfonyl cyanides using potassium hexacyanoferrate(II) as an ecofriendly cyanide source". . p. 374 - 378. Retrieved 2014/03/21.