4-(Trifluoromethylthio)benzonitrile

Base Information

• Chemical Name: 4-(Trifluoromethylthio)benzonitrile
• CAS No.: 332-26-3
• Molecular Formula: C8H4F3NS
• Molecular Weight: 203.188
• Hs Code.: 2930909899
• European Community (EC) Number: 690-001-8
• DSSTox Substance ID: DTXSID30381399
• Nikkaji Number: J3.054.885J
• Wikidata: Q72513048
• Mol file: 332-26-3.mol

Synonyms:4-(Trifluoromethylthio)benzonitrile;332-26-3;4-(trifluoromethylsulfanyl)benzonitrile;4-[(trifluoromethyl)sulfanyl]benzonitrile;4-((trifluoromethyl)thio)benzonitrile;4-[(Trifluoromethyl)thio]benzonitrile;MFCD00039475;4-TRIFLUOROMETHYLSULFANYL-BENZONITRILE;SCHEMBL516309;DTXSID30381399;BBL100660;STL554454;AKOS005255076;AS-5319;4-(Trifluoromethylthio)benzonitrile, 98%;CS-0313211;FT-0616951;4-[(trifluoromethyl)sulphanyl]benzenecarbonitrile;EN300-7399044;A821677;J-019097

Chemical Property of 4-(Trifluoromethylthio)benzonitrile

Chemical Property:

• Vapor Pressure: 0.29mmHg at 25°C
• Melting Point: 39-43 °C(lit.)
• Refractive Index: 1.535
• Boiling Point: 187.643 °C at 760 mmHg
• Flash Point: 67.285 °C
• PSA: 49.09000
• Density: 1.387 g/cm³
• LogP: 3.17018
• Sensitive.: Stench
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 203.00165479
• Heavy Atom Count: 13
• Complexity: 209

Purity/Quality:

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

4-(Trifluoromethylthio)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)SC(F)(F)F

Technology Process of 4-(Trifluoromethylthio)benzonitrile

There total 37 articles about 4-(Trifluoromethylthio)benzonitrile 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: 98.0%

tetramethylammonium trifluoromethanethiolate + 4-cyanophenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (626201-15-8) → 4-[(trifluoromethyl)sulphanyl]benzenecarbonitrile (332-26-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In toluene; at 45 ℃; Inert atmosphere;

DOI:10.1039/c5sc03359d

Reference yield: 96.0%

4-iodobenzonitrile (3058-39-7) + tetramethylammonium trifluoromethanethiolate → 4-[(trifluoromethyl)sulphanyl]benzenecarbonitrile (332-26-3)

Guidance literature:

With di-μ-iodobis(tri-t-butylphosphino)dipalladium(l); In toluene; at 80 ℃;

DOI:10.1002/anie.201501617

Reference yield: 95.0%

4-Cyanochlorobenzene (623-03-0) + tetramethylammonium trifluoromethanethiolate → 4-[(trifluoromethyl)sulphanyl]benzenecarbonitrile (332-26-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; acetonitrile; In toluene; at 20 - 45 ℃; Inert atmosphere;

DOI:10.1021/jacs.5b00538

upstream raw materials:

(trifluoromethyl)trimethylsilane

4-cyanophenylboronic acid

4-iodobenzonitrile

(2,2'-bipyride-kN₁,kN₁')(1,1,1-trifluoromethanethiolato-kS)-copper

Downstream raw materials:

4-[(trifluoromethyl)sulfonyl] benzonitrile

1-(3-{[5-Methyl-3-(3-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,2,4-oxadiazol-5-yl)-1H-pyrazol-1-yl]methyl}phenyl)piperidin-4-ol

5-(5-Methyl-1H-pyrazol-3-yl)-3-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,2,4-oxadiazole

5-[1-(3-Bromobenzyl)-5-methyl-1H-pyrazol-3-yl]-3-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,2,4-oxadiazole

Refernces

• 1、 Mudshinge, Sagar R.,Yang, Yuhao,Xu, Bo,Hammond, Gerald B.,Lu, Zhichao. "Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides". supporting information. . Retrieved 2022/02/10.
• 2、 Li, Ankun,Li, Yuxuan,Liu, Junjie,Chen, Jingqi,Lu, Kui,Qiu, Di,Fagnoni, Maurizio,Protti, Stefano,Zhao, Xia. "Metal-Free Trifluoromethylthiolation of Arylazo Sulfones". . p. 1292 - 1299. Retrieved 2021/01/14.