13343-26-5

Basic information

• Product Name: 4-CHLORO DIPHENYL SULFIDE
• Synonyms: 4-CHLORO DIPHENYL SULFIDE;4-Chlorodiphenylsulphide;1-Chloro-4-phenylsulfanylbenzene;4-Chloro diphenyl su
• CAS NO: 13343-26-5
• Molecular Formula: C₁₂H₉ClS
• Molecular Weight: 220.71786
• Mol File: 13343-26-5.mol
• Article Data: 147

Chemical Properties

• Melting Point: 62-64 °C
• Boiling Point: 339.097 °C at 760 mmHg
• Flash Point: 150.236 °C
• Appearance: /
• Density: 1.256 g/cm³
• Vapor Pressure: 0.000185mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: 4-CHLORO DIPHENYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO DIPHENYL SULFIDE(13343-26-5)
• EPA Substance Registry System: 4-CHLORO DIPHENYL SULFIDE(13343-26-5)

Safety Data

• Hazardous Substances Data: 13343-26-5(Hazardous Substances Data)

Usage

Description

4-Chloro diphenyl sulfide, with the molecular formula C12H9ClS, is a white to off-white solid chemical compound. It is insoluble in water but readily soluble in organic solvents. 4-CHLORO DIPHENYL SULFIDE is primarily recognized for its role as a building block in the synthesis of various products, including pharmaceuticals, agrochemicals, and materials. Additionally, it has been investigated for its potential in the realm of organic electronics and as an antioxidant. Due to its moderate toxicity, care must be exercised during its handling and application.

Uses

Used in Pharmaceutical Synthesis:
4-Chloro diphenyl sulfide is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 4-Chloro diphenyl sulfide is utilized as a building block for the creation of various agrochemicals, potentially enhancing crop protection and yield.
Used in Materials Science:
4-Chloro diphenyl sulfide is employed as a component in the development of new materials, leveraging its chemical properties to improve material characteristics such as stability and performance.
Used in Organic Electronics:
4-Chloro diphenyl sulfide is used as a component in the field of organic electronics, potentially contributing to the advancement of organic semiconductors and other electronic materials.
Used as an Antioxidant:
4-Chloro diphenyl sulfide is studied for its potential use as an antioxidant, which could help in preventing oxidation in various chemical and industrial processes.
Note: The specific applications and industries listed above are inferred from the general uses mentioned in the provided materials. The exact uses may vary based on further research and development in each respective field.

InChI:InChI=1/C12H9ClS/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9H

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 930-69-8 sodium thiophenolate 
• 106-39-8 bromochlorobenzene 
• 17314-33-9 tributyltin phenyl sulfide 
• 36744-94-2 C₁₂H₁₀ClNS 
• 66021-66-7 p-TolSO₂NO 
• 24702-38-3 S-(p-chlorophenyl)-S-phenyl-N-(p-tolylsulfonyl)sulfilimine 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 7727-15-3 aluminium bromide 
• 106-53-6 para-bromobenzenethiol 
• 108-90-7 chlorobenzene 
• 106-54-7 p-Chlorothiophenol 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 71-43-2 benzene 

Downstream Products

• 77785-82-1 (4-chlorophenyl)diphenylsulfonium hexafluoroantimonate 
• 80-00-2 4-Chlorophenyl phenyl sulfone 
• 5181-10-2 bis(4-chlorophenyl)sulfide 
• 75945-35-6 (±)-(4-chlorophenyl)(imino)(phenyl)-λ⁶-sulfanone 
• 2051-62-9 4'-biphenyl chloride 
• 98116-06-4 3-<4-(4-chlorophenylthio)benzoyl>acrylic acid 
• 98116-01-9 2-acetylthio-3-[4-(4-chlorophenylthio)benzoyl]propionic acid 
• 108-90-7 chlorobenzene 
• 1016-82-6 1-benzenesulfinyl-4-chloro-benzene 
• 31121-36-5 2-Chlorphenothiaphosphinsaeure 

Relevant articles and documents

Microwave-Assisted Copper Slag-Catalyzed Green S-Arylation of Arenethiols with Arylboronic Acids

Abstract: Diaryl sulfides have been synthesized in moderate to excellent yield by S-arylation of arenethiols with arylboronic acids using copper slag as a catalyst. Copper slag is a by-product obtained from smelting and refining of copper. Conventional heating method has been compared with the microwave-assisted technique. The proposed microwave-assisted synthesis provides excellent yields of diaryl sulfides in a short time (10 min) and is ligand-free, green, and cost-effective.

Copper(I) complexes with trispyrazolylmethane ligands: Synthesis, characterization, and catalytic activity in cross-coupling reactions

Three novel Cu(I) complexes bearing tris(pyrazolyl)methane ligands, Tpmx, have been prepared from reactions of equimolar amounts of CuI and the ligands Tpm, (HC(pz)3), Tpm, (HC(3,5-Me2-pz) 3), and TpmMs, (HC(3-Ms-pz)3). X-ray diffraction studies have shown that the Tpm and TpmMs derivatives exhibit a 2:1 Cu:ligand ratio, whereas the Tpm* complex is a mononuclear species in nature. The latter has been employed as a precatalyst in the arylation of amides and aromatic thiols with good activity. The synthesis of a TpmCu(I)-phthalimidate, a feasible intermediate in this catalytic process, has also been performed. Low temperature 1H NMR studies in CDCl 3 have indicated that this complex exists in solution as a mixture of two, neutral and ionic forms. Conductivity measurements have reinforced this proposal, the ionic form predominating in a very polar solvent such as DMSO. The reaction of TpmCu(I)-phthalimidate with iodobenzene afforded the expected C-N coupling product in 76% yield accounting for its role as an intermediate in this transformation.

Merging visible-light photoredox and micellar catalysis: Arylation reactions with anilines nitrosated in situ

An aqueous photocatalytic system was designed by merging visible-light photoredox catalysis with micellar catalysis. Eosin B, an organic dye, was utilized as the photocatalyst, and Triton X-100 was employed as the surfactant; both are inexpensive and commercially available. This clean and energy-saving catalytic system enables photocatalytic reactions of the diazonium ion generated in situ to proceed smoothly in water without any co-solvents or additives at room temperature.

Nickel(II) N-Heterocyclic Carbene Complexes: Versatile Catalysts for C–C, C–S and C–N Coupling Reactions

A variety of NiII complexes with a wide range of electronic and steric properties, bearing picolylimidazolidene ligands (a–g) and Cp (Cp = η5-C5H5; 2a–f) or Cp* (Cp* = η5-C5Me5; 3a, c, g) groups, have been synthesised and characterised by using NMR spectroscopy and single-crystal X-ray crystallography. The complexes have been used as precatalysts for a wide range of catalytic transformations, which most likely involve a Ni0/NiII catalytic cycle. In particular, the new well-defined 2a, 2c, 3a and 3c complexes have demonstrated great efficiency and versatility towards Suzuki–Miyaura coupling reactions, hydroamination of activated olefins and C–S cross-coupling reactions of aryl halides and thiols under mild conditions.

PREPARATION OF PHENYL ARYL SULFIDES BY REACTION OF BENZYNE WITH ETHYL ARYL SULFIDES

A variety of ethyl aryl sulfides (1) react with benzyne, with evolution of ethylene, to give phenyl aryl sulfides (3) in excellent yields, thus providing a general synthesis of 3 from arenethiols since 1 are quantitatively obtainable from arenethiols and ethyl bromide.

Palladium-catalyzed debenzylative cross-coupling of aryl benzyl sulfides with aryl bromides: Synthesis of diaryl sulfides

A novel debenzylative approach to synthesize diaryl sulfides from aryl benzyl sulfides and aryl bromides in good to excellent yields is reported. Mechanistic studies suggest a single catalyst, derived from Pd(dba)2 and NiXantPhos, efficiently catalyzes α-arylation of sulfides, C-S bond cleavage, and C-S bond formation in a tricatalytic cycle. (Chemical Equation Presented).

Hypervalent iodine in synthesis 55: An efficient method for synthesis of aryl sulfides by palladium-catalyzed reaction of hypervalent iodonium salts with mercaptans

The synthesis of aryl sulfides was carried out in high yields by the palladium-catalyzed cross-coupling reaction of diaryliodonium salts with mercaptans at room temperature in THF.

A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols

We report an exceptionally mild, general and efficient copper catalyzed cross coupling reaction of aryl bromides and thiols using 0.5 mol % CuI and 1 mol % benzotriazole. Experimental simplicity, generality, functional group tolerance and low cost of the catalyst are advantages of the protocol.

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.

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.