7570-92-5

Usage

Uses

Used in Chemical Synthesis:
(Cyclohexylsulfanyl)benzene is used as a building block in the chemical synthesis industry for creating a wide range of products. Its unique structure allows it to be a versatile component in the development of new compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (cyclohexylsulfanyl)benzene is utilized as a key component in the production of various drugs. Its chemical properties make it a valuable asset in the synthesis of medicinal compounds.
Used in Dye Manufacturing:
(Cyclohexylsulfanyl)benzene is employed as a crucial ingredient in the manufacturing of dyes. Its chemical structure contributes to the color and stability of the dyes produced.
Used in Pesticide and Fungicide Formulation:
(cyclohexylsulfanyl)benzene is also used as an active ingredient in the formulation of insecticides and fungicides. Its properties help in controlling and preventing the growth of pests and fungi that can damage crops and other plants.
Used in Organic Synthesis as a Reagent:
(Cyclohexylsulfanyl)benzene serves as a reagent in organic synthesis, facilitating various chemical reactions and contributing to the formation of desired products.
Caution:

Upstream product

• 108-85-0 1-bromocyclohexane 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 110-83-8 cyclohexene 
• 14204-24-1 N-(phenylthio)succinimide 
• 108-93-0 cyclohexanol 
• 37457-08-2 cyclohexane-1,1-diylbis(phenylsulfane) 
• 108-94-1 cyclohexanone 
• 882-33-7 diphenyldisulfane 
• 626-62-0 Cyclohexyl iodide 
• 24371-94-6 cyclohexylmercury chloride 
• 1564-39-2 1-oxa-4-thiaspiro-<4,5>decan-2-one 
• 71-43-2 benzene 
• 5296-21-9 2-(phenylsulfanylmethyl)oxirane 

Downstream Products

• 100971-72-0 1-(4-cyclohexylmercapto-phenyl)-ethanone 
• 132-65-0 dibenzothiophene 
• 1569-69-3 Cyclohexanethiol 
• 874-79-3 phenyl(propyl)sulfide 
• 622-38-8 Ethyl phenyl sulfide 
• 139-66-2 diphenyl sulfide 
• 882-33-7 diphenyldisulfane 
• 1126-80-3 (n-butylthio)benzene 
• 100-68-5 methyl-phenyl-thioether 
• 1129-70-0 pentyl phenyl sulfide 
• 4922-47-8 1-(phenylthio)cyclohex-1-ene 
• 110-82-7 cyclohexane 
• 33367-88-3 S-Cyclohexyl-S-phenyl-N-(p-tolylsulfonyl)sulfoximin 
• 92-52-4 biphenyl 

Relevant academic research and scientific papers

Base-Mediated Radical Borylation of Alkyl Sulfones

A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.

Synthesis method of alkyl sulfide compound

The invention belongs to the technical field of synthesis of organic compounds, and provides a novel method for preparing an alkyl sulfide compound. According to the method, direct synthesis preparation of the thioether compound is realized by utilizing direct coupling of an organic sulfinic acid compound and alkane under acid and illumination conditions. According to the present invention, the alkane C-H bond direct thioetherification method is adopted, the reaction functional group does not need to be configured in advance, the thioether compound synthesis reaction steps are substantially shortened, the raw materials are cheap and easily available, the conditions are mild and green, the operation is simple, convenient and safe, and the good economic prospect is provided.

Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings

Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.

A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst

Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.

Clarification on the reactivity of diaryl diselenides toward hexacyclohexyldilead under light

In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6 Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy?). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C?S Formation

Sulfur-containing molecules are of utmost topical importance towards the effective development of pharmaceuticals and functional materials. Herein, we present an efficient and mild electrochemical thiolation by cross-electrophile coupling of alkyl bromide

Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants

A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (KEDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.

IPr# - highly hindered, broadly applicable N-heterocyclic carbenes

IPr (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) represents the most important NHC (NHC = N-heterocyclic carbene) ligand throughout the field of homogeneous catalysis. Herein, we report the synthesis, catalytic activity, and full structural and electronic characterization of novel, sterically-bulky, easily-accessible NHC ligands based on the hash peralkylation concept, including IPr#, Np# and BIAN-IPr#. The new ligands have been commercialized in collaboration with Millipore Sigma: IPr#HCl, 915653; Np#HCl; 915912; BIAN-IPr#HCl, 916420, enabling broad access of the academic and industrial researchers to new ligands for reaction optimization and screening. In particular, the synthesis of IPr# hinges upon cost-effective, modular alkylation of aniline, an industrial chemical that is available in bulk. The generality of this approach in ligand design is demonstrated through facile synthesis of BIAN-IPr# and Np#, two ligands that differ in steric properties and N-wingtip arrangement. The broad activity in various cross-coupling reactions in an array of N-C, O-C, C-Cl, C-Br, C-S and C-H bond cross-couplings is demonstrated. The evaluation of steric, electron-donating and π-accepting properties as well as coordination chemistry to Au(i), Rh(i) and Pd(ii) is presented. Given the tremendous importance of NHC ligands in homogenous catalysis, we expect that this new class of NHCs will find rapid and widespread application.

LIGANDS FOR TRANSITION METAL CATALYSTS

Provided herein are a new class of extremely sterically-bulky, easily prepared N-heterocyclic carbene (NHC) ligands of Formula I, or a salt, solvate, geometric isomer, or stereoisomer thereof. The ligands are readily synthetically accessible exploiting the cost-effective, modular alkylation of anilines, an industrial chemical that is available in bulk. The NHC ligands form effective catalysts with transition metals such as Pd.

COMPLEXES OF N-HETEROCYCLIC CARBENES FOR TRANSITION METAL CATALYSIS

Described herein is a new class of highly active Pd(II)-NHC complexes bearing anilines as throw-away ligands. These catalysts are well-defined, air- and moisture-stable and can be easily purified by chromatographic techniques. High activity and generality has been exemplified in the Suzuki-Miyaura cross-coupling by C-N, C-O and C-Cl cleavage. Facile syntheses of these catalysts is also described.