106-54-7

Basic information

• Product Name: 4-Chlorothiophenol
• Synonyms: Benzenethiol,p-chloro- (6CI,7CI,8CI);1-Chloro-4-mercaptobenzene;4-Chlorophenylmercaptan;4-Chlorobenzenethiol;4-Mercaptophenyl chloride;NSC 18714;NSC 229564;p-Chlorobenzenethiol;p-Chlorophenylmercaptan;p-Chlorophenylthiol;p-Chlorothiophenol;p-Mercaptochlorobenzene;Benzenethiol, 4-chloro-
• CAS NO: 106-54-7
• Molecular Formula: C₆H₅ClS
• Molecular Weight: 144.6187
• EINECS: 203-408-9
• Product Categories: Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Aromatic Phenols
• Mol File: 106-54-7.mol
• Article Data: 82

Chemical Properties

• Melting Point: 49-53℃
• Boiling Point: 206.8 °C at 760 mmHg
• Flash Point: 78.6 °C
• Appearance: white to almost white crystalline solid
• Density: 1.268 g/cm³
• Vapor Pressure: 0.335mmHg at 25°C
• Refractive Index: 1.5480
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble
• PKA: pK1:5.9 (25°C)
• Water Solubility: insoluble
• BRN: 605971
• CAS DataBase Reference: 4-Chlorothiophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorothiophenol(106-54-7)
• EPA Substance Registry System: 4-Chlorothiophenol(106-54-7)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R22:; R34:
• Safety Statements: S26:; S36/37/39:; S45:
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: DC1050000
• F: 9-13-23
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 106-54-7(Hazardous Substances Data)

Usage

Description

4-Chlorothiophenol is a white to almost white crystalline solid that undergoes oxidative coupling catalyzed by iron(III)-tetra phenyl prophyrin to form disulfides. It is a chemical compound with the molecular formula C4H4ClS and is known for its various applications across different industries.

Uses

Used in Chemical Industry:
4-Chlorothiophenol is used as a chemical intermediate for the synthesis of various compounds, including poly(vinyl chloride) with halogen groups. It plays a crucial role in modifying poly(vinyl chloride) to enhance its properties and performance.
Used in Oil Industry:
In the oil industry, 4-Chlorothiophenol is utilized as an additive to improve the efficiency and performance of oil products. Its addition can lead to better lubrication, reduced wear, and increased stability of the oil.
Used in Agricultural Chemicals:
4-Chlorothiophenol is employed in the agricultural sector as a component in the formulation of various chemicals, such as pesticides and herbicides. Its incorporation can enhance the effectiveness of these chemicals in controlling pests and promoting crop growth.
Used in Plastics Industry:
As a plasticizer, 4-Chlorothiophenol is used to increase the flexibility, workability, and durability of plastics. It helps in reducing the brittleness and improving the overall performance of plastic materials.
Used in Rubber Industry:
In the rubber industry, 4-Chlorothiophenol is used as a rubber chemical to enhance the properties of rubber products. It can improve the elasticity, strength, and resistance to wear and tear of rubber materials.
Used in Dyes Industry:
4-Chlorothiophenol is utilized in the dyes industry as a component in the production of various types of dyes. Its presence can contribute to the color intensity, stability, and fastness of the dyes.
Used in Wetting Agents:
As a wetting agent, 4-Chlorothiophenol is used to reduce the surface tension of liquids, allowing them to spread more easily and wet surfaces more effectively. This property makes it useful in various applications, such as cleaning and coating processes.
Used in Stabilizers:
4-Chlorothiophenol is also used as a stabilizer in various industrial applications. It helps in preventing the degradation of materials, such as plastics and rubber, by inhibiting the effects of heat, light, and oxygen. This extends the lifespan and maintains the quality of the products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 4455, 1962 DOI: 10.1021/jo01059a081Synthetic Communications, 18, p. 575, 1988 DOI: 10.1080/00397918808064014

Hazard

Toxic by ingestion.

Purification Methods

Recrystallise the thiophenol from aqueous EtOH. The SMe ether has m 129o and the SEt ether has m 64o. [D'Sousa et al. J Org Chem 52 1720 1987, Beilstein 6 H 326, 6 I 149, 6 III 1034.]

InChI:InChI=1/C6H5ClS/c7-5-1-3-6(8)4-2-5/h1-4,8H/p-1

Upstream product

• 20114-14-1 (4-chloro-phenyl)-(2,4-dinitro-phenyl)-sulfide 
• 15151-78-7 ethyl S-(4-chlorophenyl) thiolcarbonate 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 123-75-1 pyrrolidine 
• 110-89-4 piperidine 
• 110-91-8 morpholine 
• 110-85-0 piperazine 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 110-81-6 Diethyl disulfide 
• 106-46-7 para-dichlorobenzene 
• 7755-92-2 piperazine-1-carbaldehyde 
• 2127-03-9 2,2'-dipyridyldisulphide 
• 98-66-8 4-chloro-benzenesulfonic acid 

Downstream Products

• 36155-35-8 2-[(4-chlorophenyl)sulfanyl]ethanamine 
• 6631-77-2 <4-Chlor-phenyl>-piperidinomethyl-sulfid 
• 93483-85-3 (4-chloro-phenylsulfanyl)-succinic acid 
• 6310-30-1 S-(4-chlorophenyl) furan-2-carbothioate 
• 54406-10-9 5-(4-chloro-phenylsulfanyl)-4-methyl-thiazol-2-ylamine 
• 132649-29-7 2-[(4-chloro-phenylsulfanyl)-methyl]-quinoline 
• 25935-61-9 2-[(4′-chlorophenyl)thio]-5-nitropyridine 
• 14483-78-4 1H-benzimidazol-2-ylmethyl 4-chlorophenyl sulfide 
• 77012-86-3 5-(4-chloro-phenylsulfanyl)-2-nitro-pyridine 
• 32570-48-2 2-(4-chloro-phenylsulfanyl)-5-nitro-furan 
• 26820-31-5 3-nitro-2-((4-chlorophenyl)thio)pyridine 
• 857763-49-6 2-(4-chloro-phenylsulfanyl)-3H-quinazolin-4-one 
• 100124-64-9 4-(4-chloro-phenylsulfanyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine 
• 107701-35-9 O-ethyl S-(4-chlorophenyl) thiocarbonate 

Relevant articles and documents

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High-performance sono/nano-catalytic system: Fe3O4?Pd/CaCO3-DTT core/shell nanostructures, a suitable alternative for traditional reducing agents for antibodies

Herein, a novel heterogeneous nanoscale reducing agent for antibody cleavage, made of iron oxide nanoparticles, silica network, palladium on calcium carbonate (10%), and dithiothreitol (Fe3O4?Pd/CaCO3-DTT), is presented as a substantial alternative for traditional homogeneous analogues. Conventionally, antibody fragmentation is accomplished using reducing agents and proteases that digest or cleave certain portions of the immunoglobulin protein structure to provide active thiol sites for drug tagging aims. Then, dialysis process is needed to separate excess chemical structures and purify the reduced antibody. In this work, we have made an effort to design a suitable heterogeneous tool for protein cleavage and skip the dialysis process for purification of the reduced antibody. In this regard, firstly, various preparation methods including microwave irradiation, reflux and ultrasonication have been precisely compared, and it has been proven that the best result is obtained through 10 min ultrasound (US) irradiation using an US bath with 50 KHz frequency and 200 W L?1 power density. Then, all the necessary structural analyses have been done and thoroughly interpreted for the final product. Afterward, the catalytic performance of Fe3O4?Pd/CaCO3-DTT nanoscale system in the presence of US waves (50 KHz, 200 W) has been monitored using some disulphide derivatives. The NPs could be conveniently separated from the mixture through their substantial paramagnetic property. Thus, dialysis process in which various types of membranes are used is practically jumped after the reduction process. In this work, this is clearly demonstrated that there is a constructive synergistic effect between US waves and prepared Fe3O4?Pd/CaCO3-DTT nanoscale reducing agent. Ultimately, trastuzumab (anti HER-2) antibody has been used to test the performance of the prepared Fe3O4?Pd/CaCO3-DTT NPs in a real protein reduction reaction.

Novel synthesis method for thiophenol derivative

The invention discloses a novel synthesis method for a thiophenol derivative, and belongs to the technical field of synthesis. The method comprises the steps that a diphenyl sulfide derivative of thegeneral formula II and hydrogen sulfate are adopted as raw materials, a tubular reactor is used as a reactor, and an equimolar quantitative reaction is performed under the normal pressure and the temperature of 330-350 DEG C to synthesize the thiophenol derivative of the general formula I. By adopting the method, the raw material utilization rate can reach 100%, no solvent or catalyst needs to beadopted in the reaction, the reaction temperature is low, and the product yield and purity are high.