23528-44-1

Basic information

• Product Name: 1,2-BIS(PHENYLTHIO)ETHYLENE (CIS- AND TRANS- MIXTURE)
• Synonyms: 1,2-BIS(PHENYLTHIO)ETHYLENE (CIS- AND TRANS- MIXTURE);1,2-BIS(PHENYLTHIO)ETHYLENE;1,2-BIS(PHENYLMERCAPTO)ETHYLENE;1,2-Bis(phenylthio)ethylene (cis- and trans- mixture)
• CAS NO: 23528-44-1
• Molecular Formula: C₁₄H₁₂S₂
• Molecular Weight: 244.37508
• Mol File: 23528-44-1.mol

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 166 °C / 0.8mmHg
• Flash Point: 174.417°C
• Appearance: /
• Density: 1.194g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: Refrigerator
• Solubility: soluble in Toluene
• CAS DataBase Reference: 1,2-BIS(PHENYLTHIO)ETHYLENE (CIS- AND TRANS- MIXTURE)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BIS(PHENYLTHIO)ETHYLENE (CIS- AND TRANS- MIXTURE)(23528-44-1)
• EPA Substance Registry System: 1,2-BIS(PHENYLTHIO)ETHYLENE (CIS- AND TRANS- MIXTURE)(23528-44-1)

Safety Data

• Hazardous Substances Data: 23528-44-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 4260, 1985 DOI: 10.1021/ja00300a031

InChI:InChI=1/C14H12S2/c1-3-7-13(8-4-1)15-11-12-16-14-9-5-2-6-10-14/h1-12H

Upstream product

• 53943-04-7 1-phenylsulfinyl-2-phenylthioethane 
• 540-59-0 1,2-Dichloroethylene 
• 21514-24-9 mercury thiophenolate 
• 1190-78-9 trans-β-chlorovinylmercury chloride 
• 882-33-7 diphenyldisulfane 
• 99172-76-6 phenylmercaptoacetaldehyde dimethyl acetal 
• 26620-11-1 (E)-2-chlorovinylthiobenzene 
• 108-98-5 thiophenol 
• 68001-64-9 (hex-1-ynyl)(phenyl)selane 

Downstream Products

• 35387-59-8 1,2-Bis(phenylsulfonyl)ethylene 
• 27064-03-5 S-phenyl methanethioate 
• 1940-19-8 1-vinylcyclohexanol 
• 20180-54-5 1-[(E)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol 
• 84072-32-2 1-[(Z)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol 

Relevant articles and documents

Ligand Non-innocence and Single Molecular Spintronic Properties of AgII Dibenzocorrole Radical on Ag(111)

A facile method for the quantitative preparation of silver dibenzo-fused corrole Ag-1 is described. In contrast to the saddle conformation resolved by single-crystal X-ray analysis for Ag-1, it adopts an unprecedented domed geometry, with up and down orientations, when adsorbed on an Ag(111) surface. Sharp Kondo resonances near Fermi level, both at the corrole ligand and the silver center were observed by cryogenic STM, with relatively high Kondo temperature (172 K), providing evidence for a non-innocent AgII-corrole.2? species. Further investigation validates that benzene ring fusion and molecule-substrate interactions play pivotal roles in enhancing Ag(4d(x2?y2))–corrole (π) orbital interactions, thereby stabilizing the open-shell singlet AgII-corrole.2? on Ag(111) surface. Moreover, this strategy used for constructing metal-free benzene-ring fused corrole ligand gives rise to inspiration of designing novel metal–corrole compound for multichannel molecular spintronics devices.

A recyclable biphasic system for stereoselective and easily handled hydrochalcogenations

Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, ste

Skeletal reorganization of mercaptoacetaldehyde dialkyl acetal in acid: formation of disulphide, 1,2-bis(mercapto)ethylene and 1,1,2-tris(mercapto)ethane derivatives

The reaction of mercaptoacetaldehyde dialkyl acetals 1a-c in the presence of sulfuric acid, polyphosphoric acid and zinc chloride is described. Other than the disulfide reported previously, new compounds 1,2-bis-(mercapto)ethylene, 1,2,3-tris-(mercapto)ethane and 1,2-bis-(mercapto)methane have been isolated for the first time.

Reactions of Alkylmercurials with Heteroatom-Centered Acceptor Radicals

The relative reactivities of alkylmercury halides toward PhS., PhSe., or I. decrease drastically from R = tert-butyl to R = sec-alkyl to R = n-butyl, indicative that R. is formed in the rate-determining step in the attack of these radicals upon RHgCl.The alkyl radicals thus formed will enter into chain reactions in which a heteroatom-centered radical (A.) is regenerated from substrates such as RS-SR, ArSe-SeAr, ArTe-TeAr, PhSe-SO2Ar, Cl-SO2Ph; ZCH=CHA (A = Cl, I, SPh, SO2Ph); or PhCCHA (A = I, SPh, SO2Ph). β-Styrenyl (PhCH=CHA, Ph2C=CHA) and β-phenethynyl (PhCCA) systems with A = I, Br, SO2Ph also enter into chain reactions with mercury(II) salts with the ligands PhS, PhSe, PhSO2, or (EtO)2PO.The relative reactivities of a series of reagents toward t-Bu. and of PhCH=CHA, Ph2C=CHA, and PhCCA toward c-C6H11. are reported as well as the regioselectivity of t-Bu. attack observed for 1,2-disubstituted ethylenes (ZCH=CHA) with Z and A from the group Ph, Cl, Br, I, SO2Ph, SPh, Bu3Sn.Reactions of (E)- and (Z)-PhCH=CHI or MeO2CCH=CHI with t-Bu. or c-C6H11. occurred in a regioselective and stereospecific (retention) manner.Reactions of (E)- and (Z)-ClCH=CHCl occurred in a nonstereospecific manner in which the E/Z product ratio increased with the bulk of the attacking radical.A similar effect on the E/Z product ratios was observed for (Z)-MeO2CCH=CHCl.

STEREOSPECIFIC VINYL SUBSTITUTIONS OCCURRING BY FREE RADICAL ADDITION-ELIMINATION

The free radical chain reaction between cyclohexyl-HgCl and (E) or (Z) MeO2CCH=CHSnBu3, MeO2CCH=CHI, or ClCH=CHHgCl forms MeO2CCH=CHC6H11 or ClCH=CHC6H11 in a stereospecific manner with retention of stereochemistry.