66919-99-1

Basic information

• Product Name: Benzene, 1,1'-[1,8-octanediylbis(thio)]bis-
• CAS NO: 66919-99-1
• Molecular Formula: C20H26S2
• Molecular Weight: 330.558
• Mol File: 66919-99-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[1,8-octanediylbis(thio)]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[1,8-octanediylbis(thio)]bis-(66919-99-1)
• EPA Substance Registry System: Benzene, 1,1'-[1,8-octanediylbis(thio)]bis-(66919-99-1)

Safety Data

• Hazardous Substances Data: 66919-99-1(Hazardous Substances Data)

Upstream product

• 24772-63-2 1,8-diiodooctane 
• 108-98-5 thiophenol 
• 82135-88-4 phenyltetramethylenesulfonium hexafluorophosphate 
• 4549-32-0 1,8-dibromooctane 

Downstream Products

• 72477-14-6 (AuCl)2(C₆H₅S(CH₂)8SC₆H₅) 
• 332077-43-7 1,8-dichloro-1,8-di(phenylsulfinyl)octane 
• 145917-46-0 1,8-Diphenyl-sulfonyloctan 

Relevant articles and documents

1H- And13C-NMR and electron ionization (EI) mass spectrometric study of o- And p-substituted 1,n-diarylsulfonylalkanes, XC6H4so2(CH2)nso 2C6H4X (n = 2-5, 8, 10)+

1,n-Diphenylsulfonylalkanes, PhSO2(CH2)nSO2Ph (n =2-5, 8, 10) and their o- or p-Cl or -OMe derivatives were prepared and their 1H- and 13C-NMR and EI mass spectra recorded and analyzed. The chemical shifts of the aliphatic α- and β-carbons showed a clear dependence on the o-aryl substitution, the o-Cl being the most shielding for both. Clear low-field effects were found also for the aliphatic α-protons in o-Cl and o-OMe derivatives. In case of p-OMe derivatives a palpable shielding of the aliphatic α-protons was also found similarly to the β-protons of the o-OMe derivatives. Characteristic mass spectrometric fragmentations which reflected both the influence of the aryl substitution and the length of the alkyl chain were observed and sometimes also exhibited the sulphinic acid rearrangement.

One-Electron Chemical Reductions of Phenylalkylsulfonium Salts

Twenty-two arylalkylsulfonium salts have been reduced with potassium in graphite in tetrahydrofuran and the sulfide products identified.Two trialkylsulfonium salts did not reduce under these conditions.Comparison of the sulfides from a series of monophenylalkylsulfonium salts reveals a leaving-group propensity of benzyl > secondary > primary > methyl > phenyl in a ratio of 28:(6.0 +/- 0.3):1.0:(0.53 +/- 0.09): 0.05.The cleavage ratio is shown to be independent of the electron source and the homogeneity of heterogeneity of the reaction in two cases.Multiplicative transitivity of the above ratios is not observed, although the same qualitative order is found for other comparisons.These results are interpreted in terms of the initial formation of a ?-ligand radical anion sulfonium cation, which undergoes cleavage to a carbon radical and a sulfide.This appears to be the first evidence for this type of structure in a sulfur system.Leaving-group propensities different from the above order are observed in reductions of diphenylsulfonium and benzo-fused sulfonium salts, and rationales are offered.The intermediates in these reactions appear to be different from those involved in radical additions to, or displacements on, sulfur.