42848-06-6

Usage

Uses

Used in Chemical Research:
Methyl(E)-1-propenyl sulfide is used as a research compound for studying the structure-stability relationships in unsaturated sulfur compounds. Its unique chemical properties make it a valuable tool for understanding the behavior and reactivity of similar compounds in various chemical reactions.
Used in Flavor and Fragrance Industry:
As a component of the volatile organic compounds found in onions, Methyl(E)-1-propenyl sulfide is used in the flavor and fragrance industry to recreate the characteristic aroma of onions in various products. This application allows for the creation of artificial onion flavors for the food industry, as well as the development of onion-scented products for the cosmetic and household goods markets.
Used in Agricultural Research:
Methyl(E)-1-propenyl sulfide can be employed in agricultural research to study the natural defense mechanisms of plants, such as onions, against pests and diseases. Understanding the role of Methyl(E)-1-propenyl sulfide in plant defense can lead to the development of more effective and environmentally friendly pest control strategies.
Used in Environmental Science:
In environmental science, Methyl(E)-1-propenyl sulfide can be used to study the behavior of volatile organic sulfur compounds in the atmosphere. This research can provide insights into the role of these compounds in atmospheric chemistry and their potential impact on air quality and climate change.

InChI:InChI=1/C4H8S/c1-3-4-5-2/h3-4H,1-2H3/b4-3+

Upstream product

• 10152-76-8 allylmethyl sulfide 
• 52195-40-1 Methyl (Z)-1-propenyl sulfide 
• 57093-94-4 propionaldehyde dimethyl thioacetal 
• 624-92-0 Dimethyldisulphide 
• 106-95-6 allyl bromide 
• 6943-87-9 1-(methylthio)propan-2-ol 

Downstream Products

• 10152-76-8 allylmethyl sulfide 

Relevant academic research and scientific papers

Isomerization processes in the synthesis of asymmetric allyl chalcogenides

Allyl-propenyl rearrangement (prototropic isomerization) occurs in the synthesis of allyl organyl chalcogenides in a hydrazine hydrate - KOH system with a 6 - 10-fold molar excess of KOH. Specificities of the rearrangement that depend on the nature of the chalcogen were studied.

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

Structure-Stability Relationships in Vinyl Sulfides. I. On the Stable Conformations of Vinyl Sulfides

A thermodynamic and 13C NMR spectroscopic study of the structures of the less stable rotamers of alkyl vinyl sulfides have been performed.It has been shown that the less stable rotamer of methyl vinyl sulfide has the planar s-trans configuration and the proportion of this is about 20percent.The energy difference between the planar s-cis and s-trans is about 3.5 kJ mol-1.Ethyl vinyl sulfide is almost an equimolar mixture of the planar s-cis and s-trans conformations.The 13C NMR data showed that the p-? cojugation in the compounds that could not adopt any of the planar arrangements was decreased.In alkyl 1-propenyl sulfides, the stabilizing interaction between the methyl group and the S atom cis to each other was ca.1.8 kJ mol-1.The most probable choice for the most stable conformation of di-1-propenyl sulfides is the planar (or nearly planar) s-trans,s-trans one.

The Electronic Interaction between the Methyl Group and Trigonal Carbon

The nature of the interaction between methyl and a trigonal carbon has been examined by the effect of substituents on the methyl rotational barrier.Barriers have been measured for para-substituted toluenes and for cis- and trans-substituted propenes by the motional effects of methyl rotation on dipole-dipole spin-lattice relaxation.The toluene barriers exhibit a fair correlation with ?I and a very poor one with ?R.Thus hyperconjugation cannot be a major factor in determining the methyl rotational barrier.The propene barriers, particularly in the cis series, also correlate with ?I but have a better correlation with ?R than do the toluenes.Examination of all the 13C chemical shifts showed that the rotational barriers correlate only with the ortho carbon in the toluenes and with the 2-carbon (methyl substituted) in the propenes.These results suggest that the methyl rotational barrier is primarily sensitive to the nature of the ortho C-H bond in the toluenes and the α-C-H bond in the propenes.The ?R and ?I correlations are in accord with this model, since the ortho toluene carbon cannot interact directly through resonance with the para substituent but must depend on polar interactions.In the propenes, on the other hand, electron density at the α-carbon is determined by both inductive and resonance effects.The major factor in determining these barriers is the electron density at the critical carbon center, which is the ortho carbon for the toluenes and the α-carbon for the propenes.