Bis(phenylthio)methane

Base Information

• Chemical Name: Bis(phenylthio)methane
• CAS No.: 3561-67-9
• Molecular Formula: C13H12S2
• Molecular Weight: 232.37
• Hs Code.: 29309090
• European Community (EC) Number: 222-624-4
• NSC Number: 65477
• UNII: 3EEZ74862L
• DSSTox Substance ID: DTXSID20189083
• Nikkaji Number: J183.113E
• Wikidata: Q63396512
• Mol file: 3561-67-9.mol

Synonyms:Bis(phenylthio)methane;3561-67-9;(Methylenebis(thio))bisbenzene;phenylsulfanylmethylsulfanylbenzene;Formaldehyde diphenyl mercaptal;Bis(phenyithio)methane;Benzene, 1,1'-[methylenebis(thio)]bis-;[methylenebis(thio)]bisbenzene;3EEZ74862L;EINECS 222-624-4;NSC-65477;Benzene, 1,1'-(methylenebis(thio))bis-;Diphenylthiomethane;C13H12S2;NSC65477;MFCD00003067;Di(phenylthio)methane;Bis(thiophenoxy)methane;{[(phenylsulfanyl)methyl]sulfanyl}benzene;NCIOpen2_003405;SCHEMBL777671;UNII-3EEZ74862L;[(phenylthio)methylthio]benzene;ZHUPZVIALZHGGP-UHFFFAOYSA-;DTXSID20189083;Formaldehyde diphenyl dithioacetal;Formaldehyde bis(phenylthio) acetal;AMY25148;1-{[(phenylthio)methyl]thio}benzene;NSC 65477;STK331044;AKOS015840602;C13-H12-S2;CS-W010352;1,1'-(methanediyldisulfanediyl)dibenzene;1,1'-[Methylenebis(thio)]bis[benzene];1-methylsulfanyl-2-phenylsulfanyl-benzene;AS-57676;Bis(phenylthio)methane, >=98.0% (GC);([(Phenylsulfanyl)methyl]sulfanyl)benzene #;B1444;FT-0623088;D70194;A822904;Q63396512

Chemical Property of Bis(phenylthio)methane

Chemical Property:

• Appearance/Colour: light yellow crystalline powder
• Vapor Pressure: 5.81E-05mmHg at 25°C
• Melting Point: 34-37 °C(lit.)
• Refractive Index: 1.661
• Boiling Point: 194 °C8 mm Hg(lit.)
• Flash Point: 177.8°C
• PSA: 50.60000
• Density: 1.19g/cm³
• LogP: 4.52850
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 232.03804273
• Heavy Atom Count: 15
• Complexity: 140

Purity/Quality:

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

Bis(phenylthio)methane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SCSC2=CC=CC=C2
• Uses: Bis(phenylthio)methane (PhSCH2SPh) may be used in the synthesis of the following:dihydroxy thioethers[Cu4I4{μ-PhS2CH2SPh}2]n[(η5-C5Me5)MCl2(η1-(PhS)2CH2)] (M=Rh, Ir ; C5Me5= pentamethylcyclopentadienyl)6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactoheptodialdo-1,5-pyranose diphenyl dithioacetal

Technology Process of Bis(phenylthio)methane

There total 80 articles about Bis(phenylthio)methane 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%

[C6H5S(O)CH2](1-)*Li(1+)=[C6H5S(O)CH2]Li (59501-96-1) + (C5H5)Fe[P(OC6H5)3]2Cl (84430-52-4) → ferrocene (102-54-5,55404-68-7) + bis(phenylthio)methane (3561-67-9) + 1,2-bis(phenylthio)ethane (622-20-8) + diphenyldisulfane (882-33-7) + lithium chloride

Guidance literature:

In tetrahydrofuran; mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;

DOI:10.1016/S0022-328X(00)86902-8

Reference yield: 95.0%

[C6H5S(O)CH2](1-)*Li(1+)=[C6H5S(O)CH2]Li (59501-96-1) + [(η(5)-cyclopentadienyl)Fe(CO)(P(OPh)3)(Cl)] → cyclopentadienyl iron(II) dicarbonyl dimer (38117-54-3) + bis(phenylthio)methane (3561-67-9) + 1,2-bis(phenylthio)ethane (622-20-8) + diphenyldisulfane (882-33-7) + lithium chloride

Guidance literature:

In tetrahydrofuran; mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;

DOI:10.1016/S0022-328X(00)86902-8

Reference yield: 94.0%

[C6H5S(O)CH2](1-)*Li(1+)=[C6H5S(O)CH2]Li (59501-96-1) + [(C5H5)Fe(CO)2P(C6H5)3](1+)*Cl(1-)=[(C5H5)Fe(CO)2P(C6H5)3]Cl (12100-38-8) → cyclopentadienyl iron(II) dicarbonyl dimer (38117-54-3) + bis(phenylthio)methane (3561-67-9) + 1,2-bis(phenylthio)ethane (622-20-8) + diphenyldisulfane (882-33-7) + lithium chloride

Guidance literature:

In tetrahydrofuran; mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;

DOI:10.1016/S0022-328X(00)86902-8

upstream raw materials:

ethanol

dichloromethane

sodium thiophenolate

tris-(phenylsulfanyl-methyl)-amine

Downstream raw materials:

trimethylsilane

Di(phenylthio)(propylthio)methan

cyclopentanealdehyde

1,1-Bis-(phenylthio)-butan-2-ol

Refernces

• 1、 Ielo, Laura,Pillari, Veronica,Gajic, Natalie,Holzer, Wolfgang,Pace, Vittorio. "Straightforward chemoselective access to unsymmetrical dithioacetals through a thiosulfonate homologation-nucleophilic substitution sequence". . p. 12395 - 12398. Retrieved 2020/10/30.
• 2、 Dethe, Dattatraya H.,Shukla, Manmohan,Dherange, Balu D.. "Sc(OTf)3-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source". supporting information. p. 5778 - 5782. Retrieved 2020/07/30.