2037-31-2

Usage

Uses

Used in Chemical Synthesis:
3-Chlorothiophenol is used as a chemical intermediate for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique chemical structure allows it to be a versatile building block in the development of new molecules with potential applications in various industries.
Used in Polymerization Processes:
3-Chlorothiophenol is used as a catalyst or initiator in the polymerization of methyl methacrylate, a widely used monomer for producing polymethyl methacrylate (PMMA), commonly known as acrylic or Plexiglas. Its transfer constant in this process is an important parameter for optimizing the polymerization reaction and controlling the properties of the resulting polymer.
Used in Material Science:
3-Chlorothiophenol can be used in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. Its incorporation into polymers or other materials can lead to the creation of novel composites or coatings with improved performance in various applications, including electronics, sensors, and coatings.
Used in Analytical Chemistry:
3-Chlorothiophenol can be employed as a reagent or reference compound in analytical chemistry for the detection, quantification, or characterization of other compounds. Its unique chemical properties and reactivity can be leveraged to develop new analytical methods or improve existing ones, enhancing the sensitivity and selectivity of chemical analyses.

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

Upstream product

• 848189-72-0 dithiocarbonic acid O-ethyl ester-S-(3-chloro-phenyl ester) 
• 108-42-9 3-chloro-aniline 
• 3996-38-1 [(3-chlorophenyl)sulfanyl]acetic acid 
• 19742-92-8 bis(3-chlorophenyl) disulfide 
• 55975-72-9 Ethyl-3-chlorphenyl-Disulfid 
• 100-77-6 3-chlorobenzenediazonium chloride 
• 104-86-9 4-chlorobenzylamine 
• 287471-39-0 m-chlorophenyl thiolmethylacetate 
• 2393-23-9 4-methoxy-benzylamine 
• 100-46-9 benzylamine 
• 108-37-2 1-bromo-3-chlorobenzene 
• 694-80-4 2-bromo-1-chlorobenzene 
• 2402-00-8 1-chloro-3-thiocyanatobenzene 
• 104-84-7 para-methylbenzylamine 

Downstream Products

• 57500-15-9 S-(3-chlorophenyl) ethanethioate 
• 56679-05-1 (3-chloro-phenyl)-(2,4-dinitro-phenyl)-sulfide 
• 21552-38-5 [2,5-Dichloro-4-(3-chloro-phenylsulfanylthiocarbonylamino)-phenyl]-dithiocarbamic acid 3-chloro-phenyl ester 
• 40806-13-1 1-(3-chlorophenylthio)propan-2-one 
• 104863-98-1 2-(3-Chloro-phenylsulfanyl)-1-methyl-ethylamine; hydrochloride 
• 86026-63-3 1-{2-[2-(3-Chloro-phenylsulfanyl)-ethyl]-pyrrolidin-1-yl}-ethanone 
• 141358-10-3 4-(3-chlorophenylthio)benzoic acid 
• 107165-40-2 5-Chloro-2-(3-chlorophenylthio)acetophenone 
• 20092-50-6 4-chloro-2-<(3-chlorophenyl)thio>benzoic acid 
• 121486-99-5 2-(3-chlorophenylthio)-3-(N,N-dimethylamino)acrylaldehyde 
• 141402-18-8 2-chloro-6-<(3-chlorophenyl)thio>benzoic acid 
• 4867-37-2 1-chloro-3-methylsulfanylbenzene 
• 22731-83-5 S,S-diphenylsulphoximine 
• 118736-30-4 1,1-bis(benzenesulphonyl)-4-(3-chlorobenzenethio)butane 

Relevant academic research and scientific papers

SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF

The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017

The aromatic thiol compound (by machine translation)

[A] at a high rate, and, high purity aromatic thiol compound method. [Solution] the presence of metal sulfide, with a compound represented by formula (1), by a vapor phase reaction of hydrogen sulfide, (2) an aromatic thiol compound represented by the formula manufacturing method. (R are each independently, C1 a-4 alkyl group, a hydroxyl group, amino group, cyano group, nitro group, C1 a-2 alkoxy group or a halogen atom; n is an integer of 0 - 5; X is a halogen atom)[Drawing] no (by machine translation)

Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol

A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.

The first observation of the E,Z configuration of Ar-X-N=S=N-X-Ar (X = S, Se) chains in the crystalline state

New oligomeric analogues of poly(sulfur nitride), i.e. 3-ClC 6R4-X-N=S=N-X-C6R4Cl-3 (5-8; R = H, F and X = S, Se), were synthesized and structurally characterized in the solid state by single-crystal XRD, in solution by variable-temperature NMR spectroscopy and in the gas phase with DFT/B3LYP calculations. In the crystal, compounds 5-7 display the well-known Z,Z configuration, whereas 8 (R = F, X = Se) is the first compound to display the E,Z configuration amongst twelve structurally defined Ar-X-N=S=N-X-Ar (X = S, Se) derivatives in the hydrocarbon and fluorocarbon series. Through a careful analysis of the packing schemes and the intermolecular interactions of the various compounds, an explanation of the abnormal behaviour of 8 is put forward. The unique E,Z configuration of the title compounds in the crystal is observed for Ar = 3-ClC6F 4 and X = Se - in the presence of eleven Z,Z configurations found by XRD for various Ar and X groups in the hydrocarbon and fluorocarbon series - and explained by specific intermolecular Se???Cl and F???Cl interactions. (Colour code: grey - C, green - Cl, light green - F, blue- N, orange - S, magenta - Se.)

Kinetics and mechanism of the aminolysis of thiophenyl methylacetates in acetonitrile

The aminolysis of Z-thiophenyl methylacetates (C2H5C(double bond O)SC6H4Z) with X-benzylamines in acetonitrile has been investigated at 45 °C. The reaction is found to proceed by a stepwise mechanism in which the rate-determining step is the breakdown of the zwitterionic tetrahedral intermediate, T±, with possibly a hydrogen-bonded four-center-type transition state. These mechanistic conclusions are drawn based on (i) the large magnitude of βX (= 1.2 to approximately 2.5) and βz (= -0.9 to approximately -1.5), (ii) the normal kinetic isotope effects (kH/kD?1.2) involving deuterated benzylamines (XC6H4CH2ND2), (iii) a large positive ρxz (= 2.4) and (iv) adherence to the reactivity-selectivity principle in all cases. The extremely large βX (βnuc) values can be accounted for by the loss of a strong localized cationic charge on the N atom of benzylamines in the expulsion from the T±. The pKa° (≥10.0) is high due to a large ratio of the expulsion rates of the amine (k-a) to thiophenolate (kb) (k-a/kb) from the T±.

Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis

Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acid medium. The product of oxidation is the corresponding thiophenol. The rate data of meta- and para-substituted acids have been correlated well with σI, σ°R values and the meta-compounds correlate well with F,R values. The reaction constants are negative and of smaller magnitudes. Further, the ortho-substituted acids show a good correlation with triparametric equation involving Taft's σI and σ°R and charton's steric parameter v. There is no considerable steric contribution to the total orthosubstituent effect. Based on these observations, the mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.

Oxidative Cleavage of S-Arylmercaptoacetic Acids by Sodium Perborate: Kinetic and Correlation Study

Kinetics of oxidation of twenty six S-arylmercaptoacetic acids (SAMA) (I) by sodium perborate (PB) have been studied in acid medium.The product of oxidation is the corresponding thiophenol.The rate data of meta- and para-substituted acids have been correlated with DSP equations.While the para-compounds correlate well with ?I and ?0R values, the meta-compounds correlate well with ?I and ?-R values.The reaction constants are negative and of smaller magnitudes.Further, the ortho-substituted acids show a good correlation with a triparametric equation involving Taft's ?I and ?0R and Charton's steric parameter ν.There is a considerable steric contribution to the total ortho-substituent effect.Based on these observations, mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed.

Kinetics and Mechanism of the Acid-Catalysed Hydrolysis of Benzaldehyde Diaryl Thioacetals and of Benzaldehyde S-Aryl, S-Ethyl Acetals in Aqueous Perchloric Acid

The effects on the rate of hydrolysis of changes in aryl substituents, acid concentration, temperature, and solvent isotope, show that the acid-catalysed hydrolyses of five benzaldehyde diaryl thioacetals and three benzaldehyde S-aryl, S-ethyl acetals in 2-7 mol dm-3 aqueous perchloric acid proceed via essentially A1 mechanisms.The pattern of the substituent effects found for the leaving, and remaining, S-aryl groups is similar to that found previously for leaving and remaining groups in O,O- and O,S-acetals.

Kinetic Study of Substituent Effects on the Mechanism of β-Elimination of Arenethiol from trans-2,3-Bis-(arylthio)-4-nitro-2,3-dihydrothiophenes in Toluene

The 2,3-dihydrothiophene derivatives (1b-f) readily undergo, in toluene, regiospecific tributylamine-promoted syn-elimination of arenethiol to give the 2-(arylthio)-4-nitrothiophenes (2b-f).For the rather complex kinetic behaviour displayed by each member of the series, a rationalisation is proposed based on a stability of the substrate's conjugate base sufficient to allow formation of non-negligible concentrations of an intermediate ion pair along the reaction co-ordinate.The system allows direct conclusions to be drawn concerning the leaving-group expulsion step: an advanced extent of bond cleavage between carbon and the leaving group can be postulated in the transition state.