10276-04-7

Usage

Uses

Used in Flavor and Fragrance Industry:
(3-METHYL-BUT-2-ENYLSULFANYL)-BENZENE is used as a fragrance ingredient for its pleasant aroma, making it a popular choice in the production of various scented products.
Used in Pharmaceutical Industry:
(3-METHYL-BUT-2-ENYLSULFANYL)-BENZENE is utilized in the synthesis of pharmaceuticals, where its unique chemical properties are leveraged to create new and effective medications.
Used in Organic Compound Synthesis:
(3-METHYL-BUT-2-ENYLSULFANYL)-BENZENE is also used in the synthesis of other organic compounds, where its but-2-enylsulfanyl group provides a distinct advantage in the development of novel chemical entities.

InChI:InChI=1/C11H14S/c1-10(2)8-9-12-11-6-4-3-5-7-11/h3-8H,9H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 2190-48-9 3-chloro-3-methyl-1-butene 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 870-63-3 prenyl bromide 
• 34043-60-2 α,α-dimethylallyl phenyl sulphide 
• 78-79-5 isoprene 
• 72863-21-9 (dimethyl-1,1 propene-2 yl) sulfonyl-1 methyl-4 benzene 
• 2973-86-6 lithium thiophenoxide 
• 59384-25-7 thiophenylmagnesium bromide 
• 38442-51-2 tert-butylmercury chloride 
• 115-18-4 2-methyl-3-buten-2-ol 
• 37605-43-9 3-methyl-1-(phenylsulfinyl)buta-1,2-diene 

Downstream Products

• 21213-23-0 2,7-Dimethyl-4-phenylmercapto-octadien-(2,6) 
• 37987-31-8 3,3-dimethyl-4,4-bis-phenylsulfanyl-but-1-ene 
• 69745-56-8 4-methyl-N-(2-methylbut-3-en-2-yl)-N-(phenylthiol)benzenesulfonamide 
• 21213-19-4 3-Methyl-1-phenylmercapto-buten-⁽²⁾ 
• 21213-21-8 2-Methyl-4-phenylmercapto-heptadien-(2,6) 
• 21213-20-7 (4-Methyl-pent-3-en-2-yl)-phenylsulfid 
• 108970-09-8 (E)-3-Hydroxy-4,4-dimethyl-1-phenyl-1,5-hexadiene 
• 84473-47-2 Phenyl thioester of 2-Chloro-3,3-dimethyl-4-pentenoic acid 
• 83577-62-2 (2,2-Dimethyl-but-3-enylsulfanyl)-benzene 
• 83577-68-8 (1,2,2-Trimethyl-but-3-enylsulfanyl)-benzene 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 83877-61-6 1-cyclohexyl-2,2-dimethyl-4-phenylthio-3-buten-1-ol 
• 124154-59-2 2,2-dimethyl-1-(4-methoxyphenyl)-3-buten-1-ol 
• 71987-46-7 1,1-Bis(phenylthio)-2-isobutylen-1-ylcyclopropan 

Relevant academic research and scientific papers

Mechanical stirring speed in water/hexane biphasic catalyst controls regioselectivity of Pd-catalyzed allylation reaction

Vigorous mechanical mixing of the water/hexane biphasic Pd-catalyzed allylation of benzenethiol gave sterically congested allyl sulfides, due to high reactivity of the enforced orientation of the η1-allylpalladium intermediate at the solvent in

Aromatic allylsulfenylation with in situ generated allyl thiols under the Heck conditions

By the catalysis of palladium(0), S-allyl thiocarbamates 1 react with aryl iodides and vinyl bromides to give allyl aryl sulfides and allyl vinyl sulfides, respectively, in good yields.

Intermolecular Pummerer Coupling with Carbon Nucleophiles in Non-Electrophilic Media

A new Pummerer-type C?C coupling protocol is introduced based on turbo-organomagnesium amides, which unlike traditional Pummerer reactions, does not require strong electrophilic activators, engages a broad range of C(sp3)-, C(sp2)-, and C(sp)-nucleophiles, and seamlessly integrates with C?H and C?X magnesiation. Given the central character of sulfur compounds in organic chemistry, this protocol allows access to unrelated carbonyls, olefins, organometallics, halides, and boronic esters through a single strategy.

Low pressure hydrogenation of unsaturated sulphides with homogeneous and heterogeneous ruthenium catalysts

Ru2O·nH2O and [Ru3O(AcO)6(H2O)3]+AcO- were examined for catalytic activity in the hydrogenation of a series of unsaturated sulphides under heterogeneous and homogeneous conditions, respectively. By the appropriate combination of these two methodologies, a number of saturated sulphides could be synthesized in satisfactory to good yields, thus minimizing side reactions.

Yb(iii)-catalysedsyn-thioallylation of ynamides

Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.

Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity

The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).

A General Photocatalytic Route to Prenylation

Prenylation is an essential reaction on which nature relies to modify properties of molecules and build terpenoids, but remains a challenging chemical reaction. Aiming to capitalize on recent advances in photocatalysis to easily and cleanly generate a broad range of carbon based radicals, we have developed a prenyl transfer reagent that is captured by transiently generated radicals. The reagent can be made in bulk, is bench stable, and broadly applicable such that it can be used with existing photocatalytic methods with very few changes to reaction conditions. Ultimately, this provides a true drop-in solution for prenylation, expanding the scope of substrates that can be readily prenylated.

Boron Lewis Acid-Catalyzed Regioselective Hydrothiolation of Conjugated Dienes with Thiols

A transition-metal-free hydrothiolation of 1,3-dienes for the synthesis of secondary and tertiary allylic sulfides is reported. The boron Lewis acids tris(pentafluorophenyl)borane, B(C6F5)3, and BF3·Et2O are shown to catalyze the regioselective hydrothiolation of a wide range of terminal 1-aryl-1,3-dienes. In the case of internal 1,3-dienes, B(C6F5)3 is by far the better catalyst than BF3·Et2O. The process features mild reaction conditions, broad scope, and low catalyst loading, and it can be scaled up quickly over a short reaction time. The reactions are rate-limited by the 1-aryl-directed protonation of 1,3-dienes with thiol-boron Lewis acid complexes, followed by sulfide anion transfer to the resultant allyl cations, as revealed by high-level DFT calculations.

Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements

A mild hemin catalytic system for sulfonium ylide generation via a metal carbenoid and a subsequent [2,3]-sigmatropic rearrangement reaction in aqueous solvent is well-established, with the assistance of cyclodextrin (CD) and Triton X-100. The protocol displays high catalytic activity with a broad substrate scope of aryl/alkyl allyl sulfides and diazo reagents, affording homoallyl sulfide products in up to 99% yield. Notably, this catalytic system is successful for water-insoluble allyl sulfides but ineffective for allyl amines or allyl ethers. Moreover, an unprecedented cascade reaction of sulfonium ylide formation, [2,3]-sigmatropic rearrangement and C-H insertion was reported.

Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.