31562-40-0

Basic information

• Product Name: (S)-(-)-TERT-BUTYL TERT-BUTANETHIOSULFINATE
• Synonyms: Aids126702;Aids-126702;Nsc122681;S-(tert-Butyl) 2-methyl-2-propanesulfinothioate
• CAS NO: 31562-40-0
• Molecular Formula: C₈H₁₈OS₂
• Molecular Weight: 194.3579
• Mol File: 31562-40-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: <21 °C
• Boiling Point: 272.5 °C at 760 mmHg
• Flash Point: 118.6 °C
• Appearance: /
• Density: 1.055 g/cm³
• Vapor Pressure: 0.0101mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: (S)-(-)-TERT-BUTYL TERT-BUTANETHIOSULFINATE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-TERT-BUTYL TERT-BUTANETHIOSULFINATE(31562-40-0)
• EPA Substance Registry System: (S)-(-)-TERT-BUTYL TERT-BUTANETHIOSULFINATE(31562-40-0)

Safety Data

• Hazardous Substances Data: 31562-40-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 3631, 1983 DOI: 10.1016/S0040-4039(00)88187-3

InChI:InChI=1/C8H18OS2/c1-7(2,3)10-11(9)8(4,5)6/h1-6H3

Upstream product

• 62383-66-8 tert-butylsulfenic tert-butylsulfinic dithioanhydride 
• 1608484-72-5 (R)-N-((S)-(2-(methoxymethoxy)phenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamide 
• 116249-84-4 2-pyridyl tert-butyl sulfoxide 
• 100-58-3 phenylmagnesium bromide 
• 594-19-4 tert.-butyl lithium 
• 110-06-5 di-tert-butyl disulfide 
• 75-66-1 2-methylpropan-2-thiol 
• 113548-13-3 N-(benzenesulfonyl)-3-phenyloxaziridine 

Downstream Products

• 31172-01-7 acetyl t-butyl disulfide 
• 64818-61-7 (tert-butylsulfinyl)cyclohexane 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 
• 7205-74-5 1-methoxy-4-(2-methyl-propane-2-sulfinyl)-benzene 
• 62076-10-2 (tert-butylsulfinyl)benzene 
• 1605-73-8 t-Butyl radical 
• 115-11-7 isobutene 
• 252897-89-5 C₄H₁₀OS₂ 
• 26756-22-9 Benzyl tert-butyl sulfoxide 
• 7417-73-4 benzyl t-butyl sulfide 
• 1361250-95-4 (tert-butylsulfinyl)(tert-butylthio)methylbenzene 
• 23837-50-5 benzaldehyde tert-butylthioacetal 
• 1173095-19-6 C₂₂H₃₀N₂O₂S 
• 102-54-5 ferrocene 

Relevant articles and documents

Iodine mediated deprotection of N-tert-butanesulfinyl amines: A functional group compatible method

In the presence of iodine, a functional group compatible method for the deprotection of tert-butanesulfinyl and p-toluenesulfinyl units was developed. This journal is the Partner Organisations 2014.

Extremely Facile Ligand-Exchange and Disproportionation Reactions of Diaryl Sulfoxides, Selenoxides, and Triarylphosphine Oxides with Organolithium and Grignard Reagents

Diaryl sulfoxides undergo unusually rapid ligand-exchange reaction upon treatment with organolithium reagents at -95 deg C.Optically pure phenyl p-tolyl sulfoxide (4b) reacted with organolithium reagents at the range from -20 to -95 deg C to give facile ligand-exchange and disproportionation products, i.e., diphenyl sulfoxide (7), recovered 4b, and di-p-tolyl sulfoxide (8) in a statistical ratio of 1:2:1 in quantitative yields, and the recovered 4b was completely racemized.This facile ligand exchange was observed in the similar reactions using only diaryl selenoxides and triarylphosphine oxides.The reactions of 18O-labeled phenyl p-tolyl sulfoxide (4c) with organolithium reagents gave products in a statistical ration without 18O scrambling, indicating that only the C-S bond cleavage took place under low temperature.It is suggested that the ligand exchange reactions occur by the nucleophilic attack by organolithium reagent at the sulfinyl sulfur atom, giving ?-sulfurane as an intermediate that collapses rapidly.These results suggest that the treatment of arylic sulfoxides, selenoxides, and phosphine oxides with strong bases should be effected with caution.

LIGAND EXCHANGE AND LIGAND COUPLING VIA THE ?-SULFURANE INTERMEDIATE IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS: CONVENIENT PREPARATION OF 2,2'-BIPYRIDINES

The reaction between methyl 2-pyridyl sulfoxide (1) with Grignard reagents afforded 2,2'-bipyridine (2) in moderate yield.The reaction is considered to involve initial ligand exchange to generate 2-pyridylmagnesium halide which in the subsequent step attacks the original sulfoxide to form the ?-sulfurane that undergoes ligand coupling to afford 2.The reaction of t-butyl-2-pyridyl sulfoxide (3) with C6H5MgBr, however, gave only 2-phenylpyridine (4).This may due to steric hindrance to the initial ligand exchange.Formation of 2 is a convenient process for preparation of 2,2'-bipyridines bearing various substituents.