15733-08-1

Basic information

• Product Name: Benzene, 1,1'-[(methylthio)methylene]bis-
• Synonyms: benzhydryl-methyl sulfide;Methyl-diphenylmethyl-sulfid;Benzhydryl-methyl-sulfid;Methylmercapto-diphenyl-methan;diphenylmethyl methyl sulfide
• CAS NO: 15733-08-1
• Molecular Formula: C14H14S
• Molecular Weight: 214.331
• Mol File: 15733-08-1.mol

Chemical Properties

• Melting Point: 33 °C
• Boiling Point: 140 °C (2 mmHg)
• Density: 1.071±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzene, 1,1'-[(methylthio)methylene]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[(methylthio)methylene]bis-(15733-08-1)
• EPA Substance Registry System: Benzene, 1,1'-[(methylthio)methylene]bis-(15733-08-1)

Safety Data

• Hazardous Substances Data: 15733-08-1(Hazardous Substances Data)

Usage

Uses

Used in the Chemical Industry:
Benzene, 1,1'-[(methylthio)methylene]bisis used as a synthetic intermediate for the preparation of Thiols and Thioethers. It serves as a key building block in the synthesis of these compounds through reduction or methylation of Thiones with Lithium Diisopropylamide (LDA). Thiols and Thioethers are important in various applications, including pharmaceuticals, agrochemicals, and materials science, due to their unique chemical properties and reactivity.
In the Pharmaceutical Industry:
Benzene, 1,1'-[(methylthio)methylene]biscan be utilized in the development of new drugs, as Thiols and Thioethers are often found in biologically active molecules. The compound's role in the synthesis of these moieties makes it a valuable asset in the design and production of novel pharmaceuticals.
In the Agrochemical Industry:
The compound is also used in the synthesis of agrochemicals, where Thiols and Thioethers can be employed as pesticides, herbicides, or other crop protection agents. The unique properties of these compounds allow them to interact with target organisms in specific ways, making them effective tools in agriculture.
In the Materials Science Industry:
Benzene, 1,1'-[(methylthio)methylene]biscontributes to the development of new materials by enabling the synthesis of Thiols and Thioethers, which can be used to create advanced polymers, coatings, and other materials with unique properties. These materials can find applications in various industries, such as electronics, automotive, and aerospace.

Upstream product

• 4237-48-3 diphenylmethanethiol 
• 74-88-4 methyl iodide 
• 74-93-1 methylthiol 
• 908093-98-1 diazodiphenylmethane 
• 75-18-3 dimethylsulfide 
• 624-92-0 Dimethyldisulphide 
• 6317-10-8 2,2-diphenyl-1,3-dithiolane 
• 2863-45-8 benzhydryl methyl sulfoxide 
• 92548-83-9 2,2-diphenyl-1,3-dithiolane S-oxide 
• 91-01-0 1,1-Diphenylmethanol 
• 67-68-5 dimethyl sulfoxide 
• 1450-31-3 Thiobenzophenon 
• 80-48-8 methyl p-toluene sulfonate 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 25195-40-8 (methylsulfonyl)diphenylmethane 
• 602-15-3 9,10-diphenylphenanthrene 
• 2863-45-8 benzhydryl methyl sulfoxide 

Relevant articles and documents

Electron transfer in the peroxytrifluoroacetic acid-assisted sulfoxidation and oxidative destruction of benzhydryl sulfides

The reactions of benzhydryl sulfides Ph2CHSCH2R (R = H, CONH2, COOH, CN) with peroxytrifluoroacetic acid in CF 3COOH were studied experimentally and by the quantum chemical density functional theory (DFT) method and exhibited an unusual dependence on the substituent R. When R≠H, a complicated oxidative destruction of the substrates occurs to form 2,4,6-tribenzhydrylphenol as one of the products, while in the case of R = H, the starting benzhydryl sulfide is smoothly sulfoxidated. This fact is due to the common electron transfer from the substrate to reagent at the initial step and the difference in subsequent transformations of the species formed.

Lithium diisopropylamide (LDA) as an efficient reducing agent for thioketones - Mechanistic consideration

Treatment of thiocarbonyl compounds with excess of lithium diisopropylamide (LDA) leads to corresponding thiols or sulfides depending on the work-up procedure. The mechanistic scenario for this unusual reduction pathway is discussed.

Reduction of thiocarbonyl compounds with lithium diisopropylamide

Treatment of 4,4-disubstituted 2-phenyl-1,3-thiazole-5(4H)-thiones with lithium diisopropylamide (LDA; LiNiPr2) in THF at -78° yielded the corresponding 1,3-thiazole-5(4H)-thioles in moderate yields. Sequential treatment with LDA and

Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4- benzoquinone oxidation under mild conditions

The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction betwee

Reactions between Grignard Reagents and Thiocarbonyl Compounds: A Revisitation

The radical anions from thiobenzophenone, thiobenzoyltriphenylsilane, and 3,5-di-tert-butylthio- benzoyltriphenylsilane were detected by EPR spectroscopy when these compounds were reacted with a number of Grignard reagents, RMgBr. The radical adducts resulting from addition of R radicals to the thiones were also detected. The formation of the radical anions indicates unambiguously the occurrence of a SET process which might be the initial stage of these reactions. In the case of tris(trimethylsilyl)ethanethial only the radical adducts were detected. The first reduction potentials of these thiones have also been measured in order to verify the feasibility of the SET process. In agreement with the EPR experiments, the calculated standard free energy changes suggest that electron transfer is possible in the first three cases and disfavored with the thioaldehyde.

Reactions of Triplet Carbenes with Sulfides and Disulfides: Ylide vs. Radical Formation

The reactions between triplet diphenylcarbene and fluorenylidene with a variety of sulfides and disulfides were investigated with use of electron paramagnetic resonance (EPR) spectroscopy, laser flash photolysis, and product studies.Diphenylcarbene reacted with these substrates by a radical-like displacement mechanism.Rate constants were ca. 1E6 M-1 s-1, and the resulting thio-substituted diphenylmethyl radicals were identified by their EPR and optical spectra.By contrast, the analogous reactions of fluorenylidene had rate constants of 1E8-1E9 M-1 s-1 and proceeded by an ylide mechanism.Product studies were consistent with these results but were not sufficient in themselves to reveal these mechanistic differences.

The Lithium Diisopropylamide-Induced Fragmentation of 2,2-Diphenyl-1,3-dithiolane S-Oxide and Several 2,2-Diaryl-1,3-dithiolane S,S'-Dioxides

The reaction of 2,2-diphenyl-1,3-dithiolane S-oxide with lithium diisopropylamide results in fragmentation to thiobenzophenone followed by further conversion leading to alkyl diphenylmethyl sulfide on trapping with alkyl halide.The reaction of 2,2-diaryl-

Reaction of Electrochemically Generated Radical Anion of Thioketone with Alkylating Agents

Electrochemically generated anion radicals of thioketones were allowed to react with alkyl halides (or tosylate).Electronic structure of the anion radical is discussed on the basis of the products.

Studies of Sulfinyl Radicals. 1. Thermal Decompositions of Benzhydryl p-Tolyl Sulfoxide and Benzhydryl Methyl Sulfoxide

The kinetics and mechanism of the thermal decompositions of benzhydryl p-tolyl sulfoxide (BTSO) and benzhydryl methyl sulfoxide (BMSO) were studied.Product analysis, ESR, and CIDNP results showed that both sulfoxides gave p-toluenesulfinyl and methanesulfinyl radicals, respectively, by the scission of carbon-sulfur bonds at 100-130 deg C.The presence of a small amount of a base such as pyridine has been found to suppress the formation of other products than the coupling products (the corresponding thiosulfonates and tetraphenylethane), which may be formed by ionic reactions of BTSO and BMSO.The mechanism of BTSO decomposition is complex, since it is in equilibrium with benzhydryl p-toluenesulfenate (BTSN) at 100-130 deg C.On the other hand, BMSO, showing simple decomposition behavior, indicated that the decomposition rates decreased on the addition of hydroxylic solvents.