107183-90-4

Basic information

• Product Name: (2E)-1-(tert-butylsulfanyl)but-2-ene
• Synonyms: trans-1-(t-Butylthio)-2-butene
• CAS NO: 107183-90-4
• Molecular Formula: C₈H₁₆S
• Molecular Weight: 144.2776
• Mol File: 107183-90-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 178.5°C at 760 mmHg
• Flash Point: 50.7°C
• Density: 0.857g/cm³
• Vapor Pressure: 1.33mmHg at 25°C
• Refractive Index: 1.472
• CAS DataBase Reference: (2E)-1-(tert-butylsulfanyl)but-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(tert-butylsulfanyl)but-2-ene(107183-90-4)
• EPA Substance Registry System: (2E)-1-(tert-butylsulfanyl)but-2-ene(107183-90-4)

Safety Data

• Hazardous Substances Data: 107183-90-4(Hazardous Substances Data)

Upstream product

• 121222-73-9 tert.-Butyl--sulfid 
• 4784-77-4 (E/Z)-crotyl bromide 
• 75-66-1 2-methylpropan-2-thiol 
• 107183-91-5 (Z)-1-(t-butylthio)but-2-ene 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 29364-29-2 sodium tert-butyl thiolate 

Downstream Products

• 107183-91-5 (Z)-1-(t-butylthio)but-2-ene 

Relevant articles and documents

A 1H and 13C NMR Study of the Structure of Sulfur-Stabilized Lithiated Allylic Carbanions

NMR studies of the solution structures of lithiated (E)-1-(t-butylthio)but-2-ene (4) and lithiated (E)-1-(phenylthio)but-2-ene (6) are reported.The structure of lithiated (E)-1-(t-butylthio)but-2-ene (4) is best described as a transoid carbanion with the allylic carbons C1, C2, and C3 having intermediate sp2-sp3 hybridization.In (4) the heteroatom and non-allylic substituent do not play any significant role in carbanion stabilization.Lithiated (E)-1-(phenylthio)but-2-ene (6) differs from (4) in that it exhibits cis geometry about the C1-C2 bond and the phenylthio group participates in helping to stabilize allylic charge.There is a discrepancy between the geometry about the C1-C2 bond in the solution and solid structures of (4) in the presence of TMEDA.

Structure-Stability Relationships in Vinyl Sulfides. III. Stabilization Caused by Different Alkylthio and Phenylthio Groups Attached to an Olefinic Double Bond

The stabilization energies of different alkylthio and phenylthio groups attached to an olefinic double bond have been evaluated with respect to the energy differences of the isomerization reactions of some unsaturated sulfides, in which the double bond migrates from the β,γ- to the α,β-position.According to these results the stabilization energies (in kJ mol-1) are: MeS 15.6, EtS 14.8, i-PrS 15.7, t-BuS 17.5 and PhS 14.4

Application du rearrangement de Claisen aux -1 alcen-1(Z) ols-3. Syntheses d'alcadien-2(E),4(E) oates d'ethyle et de (p.toluenesulfonylamino)-5 alcen-3(E) ols-1

The acid catalysed reaction between 1--1(Z)-alken-3-ols 1 and ethyl orthoacetate takes place via a Claisen rearrangement to give stereoselectively the ethyl-3-(1',1'-dimethylethyl)thio-4(E)-alkenoates 2a, b, c.Oxone oxidation converts these sulfide-esters 2 into the corresponding sulfone-esters 6a, b, c, which on treatment with sodium carbonate give the ethyl 2(E),4(E) alkadienoates 7a, b, c.Treatment of the sulfide-esters 2 with chloramine T yields compounds 10a, b, c through a sigmatropic rearrangement of the intermediate N-tosyl-sulfimines.These compounds 10 are reduced by DIBAL-H to the 5-(p.toluenesulfonylamino)-3(E) alken-1-ols 11a, b, c.