85609-03-6

Usage

Uses

Used in Polymer and Plastics Industry:
4-tert-Butyldiphenyl sulfide is utilized as a heat stabilizer for polymers and plastics, serving to prevent degradation and discoloration that can result from exposure to heat and ultraviolet radiation. Its inclusion in these materials ensures their durability and longevity under various environmental conditions.
Used in Lubricant Industry:
As a high-temperature lubricant additive, 4-tert-Butyldiphenyl sulfide contributes to the performance of lubricants, particularly in conditions where high temperatures are encountered. Its thermal stability aids in maintaining the lubricating properties of the formulation, reducing wear and tear on machinery.
Used in Chemical Synthesis:
4-tert-Butyldiphenyl sulfide is employed in the synthesis of other organic compounds, acting as a key intermediate in the production of various chemical products. Its versatility in chemical reactions makes it a valuable component in the creation of a range of specialty chemicals.

InChI:InChI=1/C16H18S/c1-16(2,3)13-9-11-15(12-10-13)17-14-7-5-4-6-8-14/h4-12H,1-3H3

Upstream product

• 30506-33-3 1-ethylsulfanyl-4-(1,1-dimethylethyl)benzene 
• 118-92-3 anthranilic acid 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 108-98-5 thiophenol 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 882-33-7 diphenyldisulfane 
• 591-50-4 iodobenzene 
• 2396-68-1 4-t-butylbenzenethiol 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 13894-14-9 4-(tert-butyl)benzenesulfenyl chloride 
• 100-58-3 phenylmagnesium bromide 
• 3972-56-3 4-(tert-butyl)chlorobenzene 
• 123324-71-0 p-tert-butylphenylboronic acid 

Downstream Products

• 833-50-1 2-phenylbenzo[d]oxazole 
• 5998-50-5 2-(4-(tert-butyl)phenyl)benzo[d]oxazole 
• 101431-40-7 1-(tert-butyl)-4-(phenylsulfonyl)benzene 

Relevant academic research and scientific papers

Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction

This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.

Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

2-Sulfoximidoyl acetic acids from multicomponent petasis reactions and their use as building blocks in syntheses of sulfoximine benzodiazepine analogues

Upon application of a multicomponent Petasis reaction, a broad range of NH-sulfoximines and boronic acids react with glyoxalic acid to afford the corresponding 2-substituted acetic acids with N-bound sulfoximidoyl groups. The protocol features excellent y

Aryl thioether compound and preparation method thereof

The invention discloses an aryl thioether compound and a synthesis method thereof, wherein an aryl carboxylic acid and a mercaptan (phenol) are used as main raw materials, and a nickel catalyst is prepared. Under the action of the phosphine ligand and the additive, the aryl carboxylic acid and the thiol (phenol) react in an organic solvent, and after the reaction is finished, the corresponding aryl thioether is obtained. The method has the advantages of low cost, high yield, simple and convenient operation, no pollution and the like, and has potential industrial application prospects. The method provides a cheap and green way for preparation of aryl thioether compounds.

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.

Generation of Aryllithium Reagents from N -Arylpyrroles Using Lithium

Treatment of 1-aryl-2,5-diphenylpyrroles with lithium powder in tetrahydrofuran at 0 °C results in the generation of the corresponding aryllithium reagents through reductive C-N bond cleavage.

A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling

An operationally simple mechanochemical C-S coupling of aryl halides with thiols has been developed. The reaction process operates under benchtop conditions without the requirement for a (dry) solvent, an inert atmosphere, or catalyst preactivation. The reaction is finished within 3 h. The reaction is demonstrated across a broad range of substrates; the inclusion of zinc metal has been found to be critical in some instances, especially for coupling of alkyl thiols.

Preventing Pd-NHC bond cleavage and switching from nano-scale to molecular catalytic systems: Amines and temperature as catalyst activators

Many reactions catalyzed by Pd complexes with N-heterocyclic carbene (NHC) ligands are performed in the presence of amines which usually act as coupling reagents or mild bases. However, amines can react with Pd/NHC complexes in a number of ways: enhancing molecular catalysis, causing the catalyst deactivation or triggering the ligandless modes of catalysis by producing NHC-free active palladium species. This study gains insight into conditions required for the efficient use of amines as activators of molecular Pd/NHC catalysis and preventing the undesirable reductive cleavage of the Pd-NHC bond in catalytic systems. Reactions of Pd/NHC complexes with various amines within a temperature range of 25-140 °C and thermal stability of the resulting amino-complexes are examined. The results indicate the major influence of the amine structure and reaction temperature on the catalyst transformation. In particular, thermal decomposition of Pd/NHC complexes with aliphatic amine ligands predominantly leads to reductive Pd-NHC bond cleavage, while deprotonation of the complexes with primary and secondary aliphatic amine ligands in the presence of strong bases at 25-60 °C promotes the activation of molecular Pd/NHC catalysis. Efficient Pd-PEPPSI complex-amine systems suitable for strong-base-promoted C-S cross-coupling reactions between aryl halides and thiols are suggested on the basis of these findings.

DABCO-promoted Diaryl Thioether Formation by Metal-catalyzed Coupling of Sodium Sulfinates and Aryl Iodides

A scalable catalytic synthesis method using commodity chemicals for constructing diaryl thioethers directly from sodium arylsulfinates and iodoarenes is reported in this study. In the presence of CuO or other copper salts such as Cu(OAc)2 as well as palladium catalysts, DABCO demonstrated to be essential to promote this transformation. Various iodoarenes and aryl sulfinates were examined and demonstrated the viability of this method. The mechanistic study showed that radical reactions occurred, while DABCO N-oxide radical can be observed by mass spectrometry. A plausible catalytic mechanism involving DABCO is also discussed, suggesting synergistic reduction of sulfinate by Cu(II) and DABCO is the key step of this coupling reaction. (Figure presented.).

Controlled Ni-catalyzed mono- and double-decarbonylations of α-ketothioesters

A method for Ni-catalyzed controlled decarbonylation of α-ketothioesters is described. Mono- and double-decarbonylations, which gave thioesters and thioethers, respectively, were selectively achieved by changing the ligand. A fundamental study of Ni-catalyzed decarbonylation of α-ketothioesters is presented.