1142-19-4

Basic information

• Product Name: 4,4'-DICHLORODIPHENYL DISULFIDE
• Synonyms: p-chlorophenyldisulfide;DI-P-CHLOROPHENYL DISULFIDE;BIS(4-CHLOROPHENYL)DISULFIDE;BIS(4-CHLOROPHENYL) DISULPHIDE;BIS(P-CHLOROPHENYL)DISULFIDE;AURORA KA-6540;4,4'-DICHLORODIPHENYL DISULFIDE;4,4'-Dichlorodiphenyl
• CAS NO: 1142-19-4
• Molecular Formula: C₁₂H₈Cl₂S₂
• Molecular Weight: 287.23
• EINECS: 214-531-2
• Product Categories: Aromatics
• Mol File: 1142-19-4.mol
• Article Data: 239

Chemical Properties

• Melting Point: 71-74 °C(lit.)
• Boiling Point: 180 °C / 2mmHg
• Flash Point: 167.843 °C
• Appearance: Colorless or light yellow liquid
• Density: 1.431 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Methanol
• BRN: 1644663
• CAS DataBase Reference: 4,4'-DICHLORODIPHENYL DISULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DICHLORODIPHENYL DISULFIDE(1142-19-4)
• EPA Substance Registry System: 4,4'-DICHLORODIPHENYL DISULFIDE(1142-19-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• RTECS: JO0766000
• TSCA: Yes
• Hazardous Substances Data: 1142-19-4(Hazardous Substances Data)

Usage

Description

4,4'-DICHLORODIPHENYL DISULFIDE, also known as Bis(4-chlorophenyl) disulfide, is a light yellow solid that can be synthesized from 4-chlorophenylthiol via oxidation. It is a key compound in the production of poly(p-phenylene sulfide) through thermolysis and can also be prepared using a microwave-assisted method involving the reaction between elemental sulfur and 1-chloro-4-iodobenzene in the presence of CuO nanopowder as a catalyst.

Uses

Used in Chemical Synthesis:
4,4'-DICHLORODIPHENYL DISULFIDE is used as a key intermediate in the synthesis of various organic compounds, including non-symmetrical heterodimer 4-chlorophenyl-2′-nitrophenyl disulfide, for its ability to react with other molecules and form new chemical entities.
Used in Polymer Production:
In the Polymer Industry, 4,4'-DICHLORODIPHENYL DISULFIDE is used as a monomer for the production of poly(p-phenylene sulfide), a high-performance thermoplastic with excellent mechanical properties, thermal stability, and chemical resistance.
Used in Microwave-Assisted Synthesis:
In the field of Green Chemistry, 4,4'-DICHLORODIPHENYL DISULFIDE is used as a reactant in microwave-assisted synthesis, which allows for faster reaction times, reduced energy consumption, and improved product yields compared to conventional heating methods.

Synthesis Reference(s)

Synthetic Communications, 10, p. 305, 1980 DOI: 10.1080/00397918008062754

Upstream product

• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 108-90-7 chlorobenzene 
• 106-46-7 para-dichlorobenzene 
• 2901-92-0 p-chlorophenylsulfinyl chloride 
• 25408-75-7 N,N'-dibenzoylsulfur diimide 
• 3839-92-7 N-benzenesulfonyl-N'-(4-chloro-phenyl)-sulfur diimide 
• 3839-91-6 N-Phenylsulfonyl-N'-p-nitrophenylsulfur diimide 
• 17197-96-5 endo-5-nitro-exo-6-phenylbicyclo<2.2.1>hept-2-ene 
• 18803-44-6 sodium p-chlorothiophenolate 
• 3405-88-7 (4-chlorophenylthio)acetic acid 
• 95-47-6 o-xylene 
• 933-01-7 4-chloro-benzenesulfenyl chloride 
• 106-42-3 para-xylene 
• 95-93-2 1,2,4,5-tetramethylbenzene 

Downstream Products

• 32884-73-4 3-((4-chlorophenyl)thio)-1H-indole 
• 16155-34-3 1-chloro-4-butylthiobenzene 
• 135707-24-3 1-(4-Chloro-phenylsulfanyl)-thianthrene 10-oxide 
• 135489-38-2 1,9-Bis-(4-chloro-phenylsulfanyl)-thianthrene 10-oxide 
• 111680-12-7 N,N'-bis(p-chlorophenylthio)-N,N'-bis(ethoxycarbonyl)hydrazine 
• 35337-68-9 4-Chloro-benzenethiol anion 
• 3226-37-7 4-chlorophenyl thiocyanate 
• 34973-39-2 1,1,3,3,4,4,-hexachloro-1-butene 
• 15446-13-6 1.1.2-Trichloro-2-4¹-chlorophenylthioaethylen 
• 88388-88-9 1,2-Dichlor-1-(4-chlor-phenylmercapto)-ethylen 
• 77922-46-4 2,2-Dichlorovinyl 4-chlorophenyl sulfide 
• 15446-12-5 1-Chloro-4-(1,2,2,2-tetrachloro-ethylsulfanyl)-benzene 
• 101414-05-5 β,β-dichloroisopropenyl p-chlorophenyl sulfide 
• 101414-11-3 1-Chloro-4-(2,3,3-trichloro-allylsulfanyl)-benzene 

Relevant articles and documents

Visible-light-mediated facile synthesis of disulfides using reusable TiO2/MoS2nanocomposite photocatalyst

A nontoxic and inexpensive TiO2/MoS2nanocomposite was prepared and employed as an efficient photocatalyst for the synthesis of symmetrical disulfides under visible light irradiation at room temperature. Both aryl and alkyl thiols survived the reaction conditions, affording the corresponding disulfides in good to excellent yields. The photocatalyst could be easily recovered by simple centrifugation and filtration and reused several times without significant loss in its activity.

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported. The procedure operates under simple conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to excellent yields. The reaction tolerates substitution in ortho-, meta- and para-substitution as well as electron-donating and electron-withdrawing groups. The S-cyclopropylation of a thiophenol was also accomplished using potassium cyclopropyl trifluoroborate.

Conversion of thiols to disulfides using a hexamethylenetetramine-bromine complex

Hexamethylenetetramine-bromine complex, a yellow-orange, very stable homogeneous solid, affects a mild and fairly general conversion of thiols to disulfides. Copyright Taylor & Francis Group, LLC.

Iron-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)?S/Se Bond Formation

The C?X (S/Se) bonds are common and ubiquitous in natural products and pharmaceuticals. Here, we report an iron-catalyzed cross-dehydrogenative coupling (CDC) reaction for the direct synthesis of C(sp3)?X (S/Se) bonds from oxindoles, phenylacetamides, pyrazolones, phenylacetonitriles and ethyl cyanoacetate with thiols and selenols. All the reactions were performed under simple and mild conditions, and air (molecular oxygen) was employed as an ideal green oxidant, thus promising broad application in chemical industry and modification of bioactive molecules. (Figure presented.).

Selective and convenient oxidation of thiols to disulfides using n-butyltriphenylphosphonium dichromate (Bun PPh3) 2Cr2O7 in solution, under solvent-free conditions and microwave irradiation

A variety of aliphatic, aromatic, and heteroaromatic thiols were rapidly and cleanly converted to their corresponding disulfides in excellent yields using n-butyltriphenylphosphonium dichromate (BTPPDC) in acetonitrile solution under solvent-free conditions and microwave irradiation. Selective oxidation of thiols in the presence of other oxidizable functional groups, such as alcohol and sulfide, is a noteworthy advantage of this method.

A direct preparation of functionalized aryl and heteroaryl disulfides from functionalized zinc organometallics by using sulfur monochloride (S 2Cl2)

A range of functionalized aryl and heteroaryl disulfides has been prepared from zinc organometallics by using sulfur monochloride (S2Cl 2). The zinc reagents were obtained by transmetalation from magnesium or lithium reagents with ZnBr2.

An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert-butyl nitrite

An efficient and convenient tert-butyl nitrite-catalyzed selective aerobic oxidation of thiols has been developed. Under the optimal reaction conditions, a number of thiol derivatives including aromatic thiols, heteroaromatic thiols and aliphatic thiols can be converted into their corresponding disulfides in good to excellent yields.

PPS Preparation. A Kinetic Study and the Effect of Water on the Polymerization

A kinetic study on poly(p-phenylene sulfide) formation from p-dichlorobenzene (1) and sodium sulfide reveals that the initiation reaction is first order with respect to 1 and sodium sulfide, respectively.Reaction on the surface of solid sodium sulfide has proved to be neglible when the reaction is carried out in the presence of the solid.The time course of the concentration of 1 and its dimer can be explained with a simplified eight step kinetic model for the initial stage, in which each of the step is first order with respect of the reactant in concern.Kineticparameters for each of the steps were estimated.Increase in / ratio causes the increase both in polymer yield and in the degree of polymerization.Presence of a small amount of water enhances considerably the rate of polymerization and increases the polymer yield, but the highest degree of polymerization was observed in the presence of water approximately equimolar to 1.

Aerobic oxidation of thioles to disulfides catalyzed by mixed-addenda vanadium (V) substituted heteropolyacids

The oxidation of thiols to related disulfides using mixed-addenda heteropolyacids as catalyst under mild condition has been studied. This system provides an efficient, convenient, and practical method for the syntheses of symmetrical disulfides. In this w

Oxidative coupling of thiols by pyridinium chlorochromate in solution and solvent free conditions

Oxidative coupling of aromatic and aliphatic thiols is achieved efficiently by pyridinium chlorochromate in solution and solvent free conditions. Omitting the solvent does not change the reaction time and product yield significantly, while the need of using the solvent is suppressed and workup procedure becomes easier.

Laccase-catalyzed in situ generation and regeneration of N-phenyltriazolinedione for the aerobic oxidative homo-coupling of thiols to disulfides

The first report on aerobic in situ generation and regeneration of N-phenyltriazolinedione, a valuable oxidizing agent, from a catalytic amount of N-phenyl urazole in the presence of a laccase enzyme is presented. The application of a 4-phenyl urazole/Laccase/O2 as a new cooperative catalytic oxidation system is reported for a transition-metal-free and halogen free oxidative homo-coupling reaction of structurally diverse thiols to their corresponding disulfides with good to excellent yields in a phosphate buffer solution under mild reaction conditions.

Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.

Supported iron oxide nanoparticles: Recoverable and efficient catalyst for oxidative S-S coupling of thiols to disulfides

Supported iron oxide nanoparticles are found to be efficient and recoverable catalyst in the selective oxidation of thiols to their corresponding disulfides using hydrogen peroxide as green oxidant at room temperature. The protocol features an easy work-up, simplicity and the utilizing mild reaction conditions, as well as high selectivity toward disulfides, are highly advantageous compared to alternative reported methodologies. The supported iron oxide nanoparticles could be easily recovered and reused several times without any loss of activity. ICP-MS results prove that there is no metal leaching observed, and demonstrating the stability of the catalyst under the reaction conditions.

Electrochemical Sulfenylation of 4-Hydroxycoumarins with Aryl Thiols Catalyzed by Potassium Iodide

A KI-catalyzed indirect electrochemical oxidative method for the synthesis of sulfenylated 4-hydroxycoumarins via cross-coupling of 4-hydroxycoumarins and aryl thiols at a low potential has been reported. The electrocatalytic activity of KI for sulfenylat

Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N-Acylsulfenamides

An efficient and eco-friendly electrochemical methodology for the oxidative cross coupling hydrogen evolution (CCHE) reactions of lactams with thiols is presented. Various electron deficient N-acylsulfenamides are smoothly produced in modest to excellent yields without using any external oxidant. Elementary mechanistic insight supports a possible free radical process and hydrogen is the only side product. This approach provides a safe, convenient, and economical preparation of synthetically important N-thiophthalimides on a gram scale.

Preparation method of symmetric disulfide bond-containing compound

The method comprises the following steps: adding a raw material and an oxidant to a reaction bottle containing a solvent; reacting 23W - 85W under the irradiation of 12 - 24h energy-saving lamps; and purifying the reaction product to obtain symmetrical disulfide bond-containing compounds. The raw material is mercaptan or thiophenol. The oxidizing agent is trichlorobromomethane, and the solvent is tetrahydrofuran. The method has the advantages of simple operation, high yield (70 - 90%), wide applicability, cheap and easily available raw materials, and provides a better way for the synthesis and production of symmetrical disulfide bond-containing compounds.