4-(Methylthio)phenylacetonitrile

Base Information

• Chemical Name: 4-(Methylthio)phenylacetonitrile
• CAS No.: 38746-92-8
• Molecular Formula: C9H9NS
• Molecular Weight: 163.243
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID10375019
• Nikkaji Number: J336.400C
• Wikidata: Q72491521
• Mol file: 38746-92-8.mol

Synonyms:38746-92-8;4-(Methylthio)phenylacetonitrile;P-(Methylthio)Phenylacetonitrile;2-(4-(methylthio)phenyl)acetonitrile;2-(4-methylsulfanylphenyl)acetonitrile;2-[4-(methylsulfanyl)phenyl]acetonitrile;4-(methylthio)benzyl cyanide;Benzeneacetonitrile, 4-(methylthio)-;p-methylthiophenylacetonitrile;P-(Methyltho)phenylacetontrle;4-Methylthiobenzeneacetonitrile;SCHEMBL3272193;DTXSID10375019;BBPATOFBGJZMJM-UHFFFAOYSA-N;MFCD01310834;[4-(methylsulfanyl)phenyl]acetonitrile;AKOS006345694;FS-1555;N-BENZYL-3,4-LUTINIDINIUMCHLORIDE;CS-0217157;FT-0676429;EN300-69548;W13500;A824269;J-523863;Z1114998149

Chemical Property of 4-(Methylthio)phenylacetonitrile

Chemical Property:

• Vapor Pressure: 0.00115mmHg at 25°C
• Melting Point: 42-43°C
• Refractive Index: 1.576
• Boiling Point: 375.3°Cat760mmHg
• Flash Point: 180.8°C
• PSA: 49.09000
• Density: 1.37g/cm³
• LogP: 2.47458
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• 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:

99.9% ^*data from raw suppliers

P-(Methylthio)phenylacetonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=CC=C(C=C1)CC#N

Technology Process of 4-(Methylthio)phenylacetonitrile

There total 10 articles about 4-(Methylthio)phenylacetonitrile 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%

potassium cyanide + 4-(methylthio)benzyl bromide (38185-19-2) → 2-[4-(methylsulfanyl)phenyl]acetonitrile (38746-92-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 16h;

DOI:10.1021/acs.orglett.1c02285

Reference yield: 89.0%

(4-bromophenyl)thioanisole (104-95-0) + ethyl 2-cyanoacetate (105-56-6) → 2-[4-(methylsulfanyl)phenyl]acetonitrile (38746-92-8)

Guidance literature:

(4-bromophenyl)thioanisole; ethyl 2-cyanoacetate; With potassium phosphate; N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(l) chloride; In ethanol; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

With water; In ethanol; at 80 ℃; Schlenk technique; Inert atmosphere; Cooling;

DOI:10.1002/anie.202014638

Reference yield: 89.0%

1-(chloromethyl)-4-methylthiobenzene (874-87-3) + sodium cyanide (143-33-9,25596-52-5) → 2-[4-(methylsulfanyl)phenyl]acetonitrile (38746-92-8)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2004.01.012

upstream raw materials:

1-(chloromethyl)-4-methylthiobenzene

sodium cyanide

4-(methylthio)benzyl alcohol

(4-bromophenyl)thioanisole

Downstream raw materials:

2-(4-methanesulfonyl-phenyl)-2-methyl-propionic acid

1-[4-(methylsulfanyl)phenyl]cyclopropanecarboxylic acid

4-(methylthio)benzoic acid

tert-butyl 4-(methylthio)benzoperoxoate

Refernces

• 1、 Delcaillau, Tristan,Woenckhaus-Alvarez, Adrian,Morandi, Bill. "Nickel-Catalyzed Cyanation of Aryl Thioethers". supporting information. p. 7018 - 7022. Retrieved 2021/09/13.
• 2、 Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei. "Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates". supporting information; experimental part. p. 4470 - 4474. Retrieved 2011/06/24.