3561-67-9

Usage

Uses

Used in Chemical Synthesis:
Bis(phenylthio)methane is used as a dithioether ligand for the synthesis of dihydroxy thioethers, which are important intermediates in the production of various organic compounds.
Used in Coordination Chemistry:
In the field of coordination chemistry, Bis(phenylthio)methane is used as a ligand to form coordination complexes with silver(I) salts. These complexes have potential applications in various areas, such as catalysis and materials science.
Used in Pharmaceutical Synthesis:
Bis(phenylthio)methane plays a crucial role in the synthesis of (-)-rasfonin, a compound with potential pharmaceutical applications. Its involvement in the synthesis process highlights its importance in the development of new drugs and therapeutic agents.
Used in the Synthesis of Specific Compounds:
Bis(phenylthio)methane is also utilized in the synthesis of specific compounds such as [Cu4I4μ-PhS2CH2SPh2]n, [(η5-C5Me5)MCl2(η1-(PhS)2CH2)], and 6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactoheptodialdo-1,5-pyranose diphenyl dithioacetal. These compounds have potential applications in various industries, including pharmaceuticals, materials science, and chemical research.

Synthesis Reference(s)

Synthetic Communications, 19, p. 31, 1989 DOI: 10.1080/00397918908050949Synthesis, p. 447, 1975 DOI: 10.1055/s-1975-23797

InChI:InChI=1/C13H12S2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h1-10H,11H2

Upstream product

• 64-17-5 ethanol 
• 75-09-2 dichloromethane 
• 930-69-8 sodium thiophenolate 
• 13084-04-3 tris-(phenylsulfanyl-methyl)-amine 
• 50-00-0 formaldehyd 
• 108-98-5 thiophenol 
• 31268-20-9 bromomethyl phenyl sulfoxide 
• 1914-64-3 Bisacetic acid 
• 75-11-6 diiodomethane 
• 7205-91-6 phenylthiomethyl chloride 
• 2372-45-4 sodium butanolate 
• 109-87-5 Dimethoxymethane 
• 2944-05-0 carbon monosulfide 
• 74-97-5 chlorobromomethane 

Downstream Products

• 3406-02-8 bis(phenylsulfonyl)methane 
• 54888-34-5 bis(phenylsulfinyl)methane 
• 54384-18-8 1-phenylsulfinyl-1-phenylsulfonylmethane 
• 56651-44-6 1,1-bis-phenylsulfanyl-pentane 
• 37891-39-7 trimethylsilane 
• 13307-63-6 α,α-Diphenyl-α-hydroxy-acetaldehyd-diphenylthioacetal 
• 58681-16-6 7,7-bis(phenylthio)bicyclo<4.1.0>heptane 
• 69036-36-8 1,1-Bis-(phenylthio)-octan-2-ol 
• 70626-86-7 Di(phenylthio)(propylthio)methan 
• 71221-29-9 4-methyl-1,1-bisphenylthiopentane 
• 94712-82-0 Caprylaldehyd-dithio-phenylacetal 
• 872-53-7 cyclopentanealdehyde 
• 16251-77-7 3-Phenylbutyraldehyde 
• 19396-83-9 norbornane-2-carboxaldehyde 

Relevant academic research and scientific papers

Scalable electrochemical reduction of sulfoxides to sulfides

A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.

Straightforward chemoselective access to unsymmetrical dithioacetals through a thiosulfonate homologation-nucleophilic substitution sequence

A sequential C1-homologation-nucleophilic substitution tactic is presented for the preparation of rare unsymmetrical dithioacetals. The judicious selection of thiosulfonates as convenient sulfur electrophilic sources - upon the homologation event conducted on an intermediate a-halothioether - guarantees the release of the non-reactive sulfonate group, thus enabling the subsequent nucleophilic displacement with an external added thiol [(hetero)- aromatic and/or aliphatic]. Uniform high yields and excellent chemocontrol were deduced during the extensive scope study, thus documenting the versatility of the direct technique for the preparation of these unique and manipulable materials.

Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals

A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alcoholic groups [(hetero)-aromatic, aliphatic] offer a convenient access to the title compounds. Genuine chemoselectivity is uniformly observed in the case of multi-functionalized systems. (Figure presented.).

Sc(OTf)3-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source

Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)3 as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.

A thioether compound and its synthetic method and application (by machine translation)

The invention belongs to the technical field of sulfur-containing organic synthesis, discloses a thioether compound and its synthetic method and application. The vinyl ether compound is acetone, b of sulfur compounds, inorganic alkali and 18 - crown ether - 6 mixing, heating and stirring, in the inorganic alkali under the action of the catalyst, the reaction under air atmosphere, and then concentrated, purified made, the vinyl ether compound of molecular formula as formula (1) as shown: Wherein R1 And R2 Selected from hydrogen atom, alkyl, alkoxy, nitro, amino, hydroxy, halogen base, acyl, aryl or a heterocyclic group. The method can avoid the toxicity is relatively large of the methylene chloride and halogenated hydrocarbon such as methylene diiodide. The synthesis step is simple, convenient and easy operation, environment friendly and under a comparatively mild condition, have high conversion, the yield of the product can be as high as 96%. The thioether compound can be applied to the production of organic synthetic intermediates in the field. (by machine translation)

Cs2CO3-promoted methylene insertion into disulfide bonds using acetone as a methylene source

An efficient halogen-free Cs2CO3-promoted methylene insertion into disulfide bonds has been achieved using acetone as a methylene source under mild conditions. This method provides a convenient and practical route to dithioacetals in up to 96% yield with good functional group compatibility.

Reduction of CO2 into Methylene Coupled with the Formation of C-S Bonds under NaBH4/I2 System

A selective four-electron reduction of CO2 with thiophenol using NaBH4 as a reductant is described to access dithioacetals. This reaction provides a novel synthetic method for the highly selective conversion of CO2 into methylene, and a new access to molecular structures via formation of C-S bonds using CO2 as the C1 source.

Regioselective transition metal- and halogen-free direct dithiolation at C(sp3)-H of nitrotoluenes with diaryl disulfides

Here we describe a potassium tert-butoxide-mediated regioselective direct C-S bond formation at the C(sp3)-H position of nitrotoluenes with disulfides in DMSO at room temperature. The developed reaction generated, in good yields, various dithioacetals having OMe, halogen, and NH2 functionalities at various positions of the arene rings of the disulfides. Interestingly, in the absence of nitrotoluene, diaryl disulfides and diselenides underwent one-carbon homologation to form dithioacetals and diselenoacetals. Synthesized dithioacetals were transformed into 4-nitrobenzaldehyde and 7-(bis(phenylthio)methyl)-1H-indole.

Photocatalytic Oxygenation of Sulfide and Alkenes by Trinuclear Ruthenium Clusters

Trinuclear Ru cluster photocatalysts that contain two Ru(II) photosensitizers and a Ru(II) reaction center are prepared, and their activity in the photocatalytic oxygenation of a sufide and alkenes is investigated. Photoirradiation (visible light) and the use of a Co salt ([Co(NH3)5Cl]Cl2, as an electron acceptor) are found to be essential for these catalytic reactions. The O atom of the water solvent (pH 6.8) is transferred to the substrate by a stepwise electron transfer and deprotonation of an aqua ligand at the reaction center. Through these processes, the aqua ligand coordinated at the reaction center is converted to a RuV=O species, which is the active intermediate in the sulfide and alkene oxygenation.

Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa-Fa?anas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.