p-Toluenesulfonylacetonitrile

Base Information

• Chemical Name: p-Toluenesulfonylacetonitrile
• CAS No.: 5697-44-9
• Molecular Formula: C9H9 N O2 S
• Molecular Weight: 195.242
• Hs Code.: 2926909090
• European Community (EC) Number: 227-173-7
• NSC Number: 125922
• UNII: 3XRA8X3VVZ
• DSSTox Substance ID: DTXSID90205547
• Nikkaji Number: J150.552A
• Wikidata: Q72495272
• Mol file: 5697-44-9.mol

Synonyms:5697-44-9;p-Toluenesulfonylacetonitrile;2-tosylacetonitrile;Tosylacetonitrile;4-Toluenesulfonylacetonitrile;[(4-Methylphenyl)sulfonyl]acetonitrile;p-Tolylsulfonylacetonitrile;4-(Methylphenyl)sulfonylacetonitrile;2-(4-methylphenyl)sulfonylacetonitrile;2-(4-methylbenzenesulfonyl)acetonitrile;Acetonitrile, [(4-methylphenyl)sulfonyl]-;(Toluene-4-sulfonyl)-acetonitrile;MFCD00039487;3XRA8X3VVZ;P-toluenesulphonylacetonitrile;4-toluenesulphonylacetonitrile;4-(Toluenesulfonyl)acetonitrile;EINECS 227-173-7;NSC-125922;p-(Cyanomethylsulfonyl)toluene;Acetonitrile, ((4-methylphenyl)sulfonyl)-;NSC125922;Maybridge3_003461;UNII-3XRA8X3VVZ;p-tolylsulphonyl-acetonitrile;SCHEMBL1169954;p-Toluenesufonyl Methylisocyanide;(toluene-4-sulfonyl)acetonitrile;BBNNLJMGPASZPD-UHFFFAOYSA-;AMY3235;DTXSID90205547;4-Methylbenzenesulfonylacetonitrile;HMS1440N07;(4-methylphenyl)sulfonylacetonitrile;STK400675;AKOS000264739;AC-1441;FS-1061;NSC 125922;IDI1_014848;[(4-Methylphenyl)sulfonyl]acetonitrile #;SY048449;A8140;BB 0219426;CS-0063812;FT-0635810;T0846;EN300-01482;Z57167805;F1085-0009;4-(Toluenesulphonyl)acetonitrile

Chemical Property of p-Toluenesulfonylacetonitrile

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Melting Point: 147-151 ºC
• Refractive Index: 1.5270 (estimate)
• Boiling Point: 400.9 °C at 760 mmHg
• Flash Point: 196.3 °C
• PSA: 66.31000
• Density: 1.24 g/cm³
• LogP: 2.37308
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 195.03539970
• Heavy Atom Count: 13
• Complexity: 298

Purity/Quality:

98%,99%, ^*data from raw suppliers

[(4-Methylphenyl)sulfonyl]acetonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,T
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of p-Toluenesulfonylacetonitrile

There total 25 articles about p-Toluenesulfonylacetonitrile 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: 100.0%

3-azido-2-methylbut-3-en-2-ol (1624363-23-0) + p-toluenesulfonyl chloride (98-59-9) → p-tolylsulfonylmethyl isocyanide (5697-44-9)

Guidance literature:

With 2,6-dimethylpyridine; tris(bipyridine)ruthenium(II) dichloride hexahydrate; In acetonitrile; at 20 ℃; for 4h; Irradiation;

DOI:10.1039/c9sc01370a

Reference yield: 93.0%

chloroacetonitrile (107-14-2) + sodium 4-methylbenzenesulfinate (824-79-3) → p-tolylsulfonylmethyl isocyanide (5697-44-9)

Guidance literature:

In various solvent(s); at 60 ℃; for 2h; other solvent;

DOI:10.1246/bcsj.57.613

Reference yield: 86.0%

toluene-4-sulfonic acid hydrazide (1576-35-8) + acetonitrile (75-05-8,26809-02-9) → p-tolylsulfonylmethyl isocyanide (5697-44-9)

Guidance literature:

With dipotassium peroxodisulfate; at 80 ℃; for 5h; Temperature;

upstream raw materials:

dibromo-(toluene-4-sulfonyl)-acetonitrile

chloroacetonitrile

sodium 4-methylbenzenesulfinate

ethanol

Downstream raw materials:

2-tosylpropionitrile

3-(toluene-4-sulfonyl)-[2]quinolylamine

4-dimethylamino-α-(toluene-4-sulfonyl)-cinnamonitrile

hydroxyimino-(toluene-4-sulfonyl)-acetonitrile

Refernces

• 1、 Efimova, Anna S.,Kutasevich, Anton V.,Kuz'Mina, Ludmila G.,Mityanov, Vitaly S.,Perevalov, Valery P.,Sizonenko, Marina N.. "Unexpected Aldehyde-Catalyzed Reaction of Imidazole N -Oxides with Ethyl Cyanoacetate". supporting information. p. 179 - 182. Retrieved 2020/01/23.
• 2、 Song, Jin-Na,Wang, Zikun,Zhang, Xueying,Zhang, Zhansong. "Reductive radical-initiated 1,2-C migration assisted by an azidyl group". . p. 7921 - 7926. Retrieved 2020/08/19.