19843-98-2

Usage

Uses

Used in the Chemical Industry:
[(Cyclohexylsulfanyl)methyl]benzene serves as a crucial solvent in various chemical processes. Its ability to dissolve a wide range of substances makes it an indispensable component in the chemical industry. It is used as a solvent for [reason for its use as a solvent, e.g., its ability to dissolve a wide range of substances].
Used in Organic Synthesis:
[(cyclohexylsulfanyl)methyl]benzene also acts as a reagent in organic synthesis, facilitating numerous chemical reactions that lead to the creation of a variety of products. [(Cyclohexylsulfanyl)methyl]benzene is used as a reagent in organic synthesis for [reason for its use as a reagent, e.g., its facilitation of various chemical reactions].
Used in the Perfume Industry:
The sweet, aromatic odor of [(cyclohexylsulfanyl)methyl]benzene makes it a desirable ingredient in the perfume industry. It is used as a base note or modifier in the creation of different fragrances to enhance their complexity and longevity. [(Cyclohexylsulfanyl)methyl]benzene is used as a component in perfumes for [reason for its use, e.g., its sweet, aromatic odor].
Used in the Flavor Industry:
Similarly, its distinctive scent and taste properties position [(cyclohexylsulfanyl)methyl]benzene as a valuable additive in the flavor industry. It can be used to impart specific flavor profiles to various food and beverage products. [(Cyclohexylsulfanyl)methyl]benzene is used as a flavoring agent for [reason for its use, e.g., its distinctive scent and taste properties].
Used in the Pharmaceutical Industry:
[(cyclohexylsulfanyl)methyl]benzene also finds application in the pharmaceutical industry, where it may be used in the development of new drugs or as an intermediate in the synthesis of existing medications. [(Cyclohexylsulfanyl)methyl]benzene is used in the pharmaceutical industry for [reason for its use, e.g., its role in drug development or synthesis].
Used in Polymer Production:
Furthermore, [(cyclohexylsulfanyl)methyl]benzene can be a precursor in the production of polymers, contributing to the development of new materials with specific properties for various applications. It is used as a precursor in polymer production for [reason for its use, e.g., its contribution to the development of new materials].
Safety Precautions:
It is important to handle [(cyclohexylsulfanyl)methyl]benzene with care, as it may pose health risks if ingested, inhaled, or comes into contact with the skin. Appropriate safety measures should be taken during its use to minimize potential hazards.

Upstream product

• 100-53-8 phenylmethanethiol 
• 110-83-8 cyclohexene 
• 10035-90-2 S-cyclohexyl benzothioate 
• 86971-27-9 2-(cyclohexylthio)benzo[d]oxazole 
• 100-44-7 benzyl chloride 
• 16131-50-3 N,N'-Dithiobis(dibenzylamine) 
• 1569-69-3 Cyclohexanethiol 
• 100-51-6 benzyl alcohol 
• 51048-30-7 (cyclohexylthio)trimethylsilane 
• 108-88-3 toluene 
• 108-85-0 1-bromocyclohexane 
• 100-39-0 benzyl bromide 
• 626-62-0 Cyclohexyl iodide 
• 766-92-7 [(methylthio)methyl]-benzene 

Downstream Products

• 34009-02-4 ((cyclohexylsulfonyl)methyl)benzene 
• 17377-30-9 alpha-(benzylmercapto)acetonitrile 

Relevant academic research and scientific papers

Photogeneration of thiyl radicals using metal-halide perovskite for highly efficient synthesis of thioethers

Recently, the use of metal-halide perovskite (MHP) for photoinduced organics transformation has attracted much attention. We report herein the development of photoinduced thiol-ene reaction using inorganic MHP of CsPbBr3 nanocrystal that is visible light-responsive, easy-to-prepare, and cost-effective. Under blue light-emitting diode (LED), a series of thiol substrates are demonstrated to be highly efficient reaction partners to couple with alkenes tolerated with various functional groups, affording diverse thioethers containing C–S bonds. The CsPbBr3-mediated thiol-ene reaction is characterized by high efficiency, broad substrate applicability, excellent yields, and mild conditions. Mechanism investigation shows that the visible light-excited CsPbBr3 induces the generation of thiyl radicals via hole oxidation to initiate the reaction, followed by redox neutral pathway and/or chain transfer pathway to accomplish thiol–olefin coupling. It is notable that CsPbBr3 exhibits advanced thiol-ene performance than that using MHP analogs and others. The work presents a new exploration of MHP-mediated transformation and shows great potential of MHPs for radical chemistry.

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.

Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis

Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.

Photoactive Metal-Organic Frameworks for the Selective Synthesis of Thioethers: Coupled with Phosphine to Modulate Thiyl Radical Generation

Metal-organic framework (MOF) materials are intriguing photocatalysts to trigger radical-mediated chemical transformations. We report herein the synthesis and characterization of a series of isomorphic MOFs which show a novel structure, wide visible-light absorption, high chemical stability, and specific redox potential. The prepared MOFs were explored for the photoinduced single-electron oxidation of thiol compounds, generating reactive thiyl radicals to afford thioethers via a convenient thiol-olefin reaction. Importantly, we provide a widely applicable strategy by combing a photoactive MOF with phosphine to modulate the generation of thiyl radical in the reaction, thereby producing a single product of the thioether without the formation of a disulfide byproduct due to the dimerization of thiyl radicals. The photocatalytic reaction takes advantage of this strategy, showing great generality where tens of thiols and olefins have been examined as coupling partners. In addition, the strategy has also been demonstrated to be effective for the reactions catalyzed by other MOFs. Mechanism studies reveal that the selective synthesis of C-S products relies on a synergy between the photoinduced generation of a thiyl radical over the MOF and the in situ cleavage of S-S bond into a S-H bond by phosphine. It is notable that the synthesized MOFs show advanced performance in comparison with classical MOFs. The work not only provides a series of novel MOF photocatalysts that are capable of photoinduced thiol-olefin coupling but also indicates the great potential of MOFs for photochemical transformations mediated by reactive radicals.

Efficient visible light initiated hydrothiolations of alkenes/alkynes over Ir2S3/ZnIn2S4: Role of Ir2S3

The hydrothiolations of alkynes/alkenes with thiols is an atom-economic and thus attractive method for the constructions of C-S bonds. Here Ir2S3/ZnIn2S4 nanocomposites with varied Ir2S3 loadings were obtained by one-pot solvothermal method from ZnCl2, InCl3 and thioacetamide with IrCl3. The loading of Ir2S3 on the surface of ZnIn2S4 promoted the hydrothiolations of alkenes and alkynes, with an optimum performance observed over 0.5 molpercent Ir2S3/ZnIn2S4 nanocomposite. Based on the studies on the performance of several other cocatalysts (MoS2, NiS and Pd) loaded ZnIn2S4 and the EIS analyses, it was proposed that the superior performance over Ir2S3/ZnIn2S4 nanocomposite can be ascribed to an improved efficiency on the photogeneration of the thiyl radicals by loading Ir2S3 as well as its inactivity for photocatalytic hydrogen evolution, a side reaction in the light initiated hydrothiolation reaction over ZnIn2S4. This study not only demonstrates an efficient and green strategy to synthesize thiolated products under visible light based on semiconductor photocatalysis, but also provides some guidances for the design and development of photocatalytic systems for light induced organic syntheses.

Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.

Bis(alkyl) scandium and yttrium complexes coordinated by an amidopyridinate ligand: Synthesis, characterization and catalytic performance in isoprene polymerization, hydroelementation and carbon dioxide hydrosilylation

New neutral bis(alkyl) Sc and Y complexes [N,Npy,N-]Ln(CH2SiMe3)2(THF)n [n = 0, Ln = Sc (1Sc), Y (1Y); n = 1, Ln = Y (1YTHF)] stabilized by a tridentate monoanionic amidopyridinate ligand were straightforwardly prepared by alkane elimination, upon mixing ligand [N,Npy,N-]H and metal precursor Ln(CH2SiMe3)3(THF)2 in toluene at 0 °C. Depending on the work-up conditions, yttrium bis(alkyl)s were isolated as either a pentacoordinate Lewis base free complex [N,Npy,N-]Y(CH2SiMe3)2 (1Y) or as a hexacoordinate THF adduct [N,Npy,N-]Y(CH2SiMe3)2THF (1YTHF). For the smaller Sc ion the only solvent-free complex [N,Npy,N-]Y(CH2SiMe3)2 (1Sc) was isolated as a pentacoordinate species irrespective of the reaction/work-up/crystallization conditions applied. Complexes 1Ln (Ln = Y, Sc) and 1YTHF were scrutinized as pre-catalysts in ternary catalytic systems Ln/borate/AliBu3 (borate = [HNMe2Ph][B(C6F5)4] or [Ph3C][B(C6F5)4]), applied to isoprene (IP) polymerization, providing moderate activity albeit high selectivity with predominant formation of 1,4-cis polyisoprene (up to 99%). The same complexes proved to be effcient catalysts also for the intermolecular hydrolelementation of styrene with various EH sustrates (pyrrolidine, morpholine, Ph2PH, PhPH2, PhSH) affording linear anti-Markovnikov addition products exclusively. After a preliminary activation by B(C6F5)3, selected bis(alkyl) complexes from this series have been finally used as valuable pre-catalysts for the CO2 hydrosylilation to CH4 in the presence of organosilanes as reducing agents (PhMe2SiH, PhSiH3, Et2MeSiH).

Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols

Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.

Metal-free photocatalytic thiol-ene/thiol-yne reactions

The organic photocatalyst (9-mesityl-10-methylacridinum tetrafluoroborate) in the presence of visible light is used to initiate thiol-ene and thiol-yne reactions. Thiyl radicals are generated upon quenching the photoexcited catalyst with a range of thiols

Visible light initiated hydrothiolation of alkenes and alkynes over ZnIn2S4

The construction of C-S bonds is very important. The hydrothiolation of alkenes or alkynes with thiols represents an attractive and atom economical approach for the formation of C-S bonds. In this manuscript, flowerlike microspheres of ZnIn2S4 consisting of interweaving nanoflakes were prepared by a solvothermal method and were applied for the first time in the visible light initiated hydrothiolation of alkenes and alkynes. The reactions between a broad range of thiols and alkynes or alkenes over irradiated ZnIn2S4 afford the corresponding hydrothiolated products in moderate to excellent yields. The mechanism proposed based on the ESR results suggests that the holes generated over irradiated ZnIn2S4 are reductively quenched by the thiols to generate thiyl radicals, which are added to the alkynes/alkenes to generate alkene/alkyl radicals for the propagation of thiol-ene/thiol-yne coupling reactions. The use of solar light and a semiconductor-based photocatalyst to realize the thiol-ene and thiol-yne coupling reactions in a green solvent (methanol), with only stoichiometric thiols required and applicable to a broad substrate scope, makes this reaction protocol a green, sustainable and cost-effective strategy for the synthesis of thiolated products. This study also highlights the great potential of semiconductor-based photocatalysis for advanced organic syntheses.