2-[(4-Methylphenyl)thio]acetonitrile

Base Information

• Chemical Name: 2-[(4-Methylphenyl)thio]acetonitrile
• CAS No.: 21681-88-9
• Molecular Formula: C9H9NS
• Molecular Weight: 163.243
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID70384107
• Wikidata: Q82176041
• Mol file: 21681-88-9.mol

Synonyms:21681-88-9;2-[(4-Methylphenyl)thio]acetonitrile;2-(p-Tolylthio)acetonitrile;2-(4-methylphenyl)sulfanylacetonitrile;Acetonitrile,2-[(4-methylphenyl)thio]-;4-methylthiophenoxyacetonitrile;Cyclohexanecarboxylicacidsodimsalt;SCHEMBL10395941;DTXSID70384107;IDNIFCMGOQTKGB-UHFFFAOYSA-N;MFCD00040706;AKOS000217099;2-(4-methylphenyl)sulfanylethanenitrile;FT-0602733;A815605;Z54591058

Chemical Property of 2-[(4-Methylphenyl)thio]acetonitrile

Chemical Property:

• Vapor Pressure: 0.00484mmHg at 25°C
• Refractive Index: 1.576
• Boiling Point: 276.3 °C at 760 mmHg
• Flash Point: 120.9 °C
• PSA: 49.09000
• Density: 1.11g/cm³
• LogP: 2.61068
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 163.04557046
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

98%min ^*data from raw suppliers

2-(p-Tolylthio)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-[(4-Methylphenyl)thio]acetonitrile

There total 12 articles about 2-[(4-Methylphenyl)thio]acetonitrile 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: 91.0%

chloroacetonitrile (107-14-2) + para-thiocresol (106-45-6) → (4-methylphenylthio)acetonitrile (21681-88-9)

Guidance literature:

With sodium methylate; In methanol; 1) r.t, 2h, 2) 50 deg C, 5 h;

DOI:10.1135/cccc19811188

Reference yield: 77.0%

2-(p-tolylthio)-2-(triphenylphosphaneylidene)acetonitrile (20728-17-0) → (4-methylphenylthio)acetonitrile (21681-88-9)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/acs.joc.1c00114

Reference yield: 73.0%

di(p-tolyl) disulfide (103-19-5) + acetonitrile (75-05-8,26809-02-9) → (4-methylphenylthio)acetonitrile (21681-88-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) -78 deg C, 2 h;

DOI:10.1039/p19960000333

upstream raw materials:

chloroacetonitrile

para-thiocresol

α-cyanomethyl p-tolyl sulphoxide

sodium p-thiocresolate

Downstream raw materials:

1-cyano-1-(p-tolylthio)cyclobutane

(E)-3-Methylsulfanyl-3-o-tolylamino-2-p-tolylsulfanyl-acrylonitrile

(4-Methyl-2-nitro-benzenesulfonyl)-acetonitrile

1--1-(p-tolylthio)cyclobutane

Refernces

• 1、 Ramirez, Nieves P.,K?nig, Burkhard,Gonzalez-Gomez, Jose C.. "Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis". supporting information. . Retrieved 2019/03/08.
• 2、 Empel, Claire,Hock, Katharina J.,Koenigs, Rene M.. "Iron-catalysed carbene-transfer reactions of diazo acetonitrile". supporting information. p. 7129 - 7133. Retrieved 2018/10/24.