17231-94-6

Usage

Uses

Used in Organic Synthesis:
3,5-Dichlorothiophenol is used as a key intermediate in the field of organic synthesis for various chemical reactions. Its high reactivity allows it to participate in a wide array of synthetic applications, making it a valuable compound in the development of new chemical products.
Used in Chemical Research:
In the realm of chemical research, 3,5-Dichlorothiophenol is employed as a model compound to study the properties and reactions of chlorophenols and thiophenols. This helps researchers understand the behavior of similar compounds and develop new synthetic strategies and applications.
Used in Pharmaceutical Industry:
3,5-Dichlorothiophenol is used as a building block in the synthesis of certain pharmaceutical compounds. Its unique structure and reactivity enable the creation of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 3,5-Dichlorothiophenol is utilized as a starting material for the synthesis of various agrochemical products, such as pesticides and herbicides. Its versatility in chemical reactions contributes to the development of effective crop protection solutions.
Used in Dye and Pigment Industry:
3,5-Dichlorothiophenol is used as a precursor in the production of certain dyes and pigments. Its chemical properties allow for the creation of a range of colors and shades, enhancing the variety of products available in the market.
Used in Material Science:
In material science, 3,5-Dichlorothiophenol is employed in the synthesis of novel materials with specific properties, such as conductivity or magnetism. Its role in the development of advanced materials contributes to the advancement of various technologies and applications.

InChI:InChI=1/C6H4Cl2S/c7-4-1-5(8)3-6(9)2-4/h1-3,9H

Upstream product

• 852719-52-9 O,O-diethyl S-(3,5-dichlorophenyl)-phosphorothioate 
• 67-56-1 methanol 
• 1455-13-6 deuteromethanol 
• 102871-54-5 3,5-dichlorophenyl benzyl thioether 
• 1236206-77-1 C₇H₇Cl₂O₂PS 
• 886227-40-3 O-ethyl S-3,5-dichlorophenyl methylphosphonothioate 
• 124-41-4 sodium methylate 
• 626-43-7 3,5-Dichloroaniline 
• 108-70-3 1,3,5-trichlorobenzene 

Downstream Products

• 21552-41-0 [2,5-Dichloro-4-(3,5-dichloro-phenylsulfanylthiocarbonylamino)-phenyl]-dithiocarbamic acid 3,5-dichloro-phenyl ester 
• 86026-61-1 1-{2-[2-(3,5-Dichloro-phenylsulfanyl)-ethyl]-pyrrolidin-1-yl}-ethanone 
• 137897-99-5 1,2-bis(3,5-dichlorophenyl)disulfane 
• 643763-08-0 2-(3,5-dichloro-phenylsulfanyl)-benzaldehyde 
• 75277-36-0 bis(1,3-dichlorobenzene)-5,5-sulfone 
• 875046-88-1 C₃₆H₂₂Cl₄O₂S₅ 
• 875046-90-5 C₄₀H₃₄O₆S₅ 
• 875046-87-0 C₃₆H₂₂F₄O₂S₅ 

Relevant academic research and scientific papers

Protease inhibitors (by machine translation)

The invention relates to a Grp94 specific Hsp - 90 inhibitor, a protease inhibitor of the preparation method, to solve the existing problems on the preparation method of the blank defect, comprising the following processing steps: in the three flasks, is put into the water-free of dimethyl formamide, under the protection of nitrogen, adding 3, 5 - dichloro dithiol, completely dissolved after stirring, then slowly adding sodium hydride, stirring at room temperature the reaction 1 hours; then and then adding 8 - bromo - 9 - (3 - isopropylamino) propyl adenine, after adding gradually raising the temperature to 150 degrees, reflux reaction for 6 hours; after the reaction is complete cooling to room temperature, the reaction liquid is slowly added to the water, quenching the unreacted sodium hydride, methylene chloride/methanol mixed solution extraction, the organic phase is used for the saturated salt water and saturated ammonium chloride solution washing several times, and then after the saturated sodium bicarbonate multi-time extraction, for water-free magnesium sulfate drying, steaming and, for column chromatography column purification. (by machine translation)

A study of the kinetics of La3+-promoted methanolysis of S-aryl methylphosphonothioates: Possible methodology for decontamination of EA 2192, the toxic byproduct of VX hydrolysis

The kinetics of the La3+-catalyzed methanolysis of a series of S-aryl methylphosphonothioates (4a-e, phenyl substituents = 3,5-dichloro, 4-chloro, 4-fluoro, 4-H, 4-methoxy) were studied at 25 °C with ss pH control. The reaction involves saturation binding of the anionic substrates to dimeric La3+/methoxide catalysts formulated as La2 3+(-OCH3)x, where x = 2-5 depending on the solution ss pH. Cleavage of the La3+-bound methylphosphonothioates is fast, ranging from 5 × 10-3 s -1 to 5.5 × 10-5 s-1 for substrates 4a-e at a ss pH of 8.4 and 1.6 × 10-1 s-1 to 4 × 10-3s-1 at a ss pH of 11.7. The rate accelerations for the methanolysis of substrates 4a-e, relative to their background methoxide-promoted reactions, average 7 × 1010 and 1.5 × 109, respectively, at sspH's of 8.4 and 11.7. The catalytic system is predicted to cleave EA 2192 (S-2(N,N-di-iso-propylaminoethyl) methylphosphonothioate), a toxic byproduct of the hydrolysis of VX, with a t1/2 between 4 and 8 min at a ss pH of 8.4, and 27 min at a ss pH of 11.7.

Catalytic decomposition of simulants for chemical warfare V agents: Highly efficient catalysis of the methanolysis of phosphonothioate esters

(Chemical Equation Presented) As good as the original: Extremely effective methanolysis of phosphonothioates using metal-containing systems (e.g., 1) was achieved. The catalytic methanolysis of a SCH2CH2NEt 2 derivative, an analogue of the organophosphorus chemical warfare material VX, was predicted, and the catalyzed methanolysis of S-(3,5-dichlorophenyl) O-ethyl methylphosphonothioate was shown to involve a concerted displacement of the aryl thioate (transition state 2)

Solvent deuterium kinetic isotope effects for the methanolyses of neutral C=O, P=O and P=S esters catalyzed by a triazacyclododecane : Zn 2+-methoxide complex

The methanolyses of several organophosphate/phosphonate/phosphorothioate esters (O, O-diethyl O-(4-nitrophenyl) phosphate, paraoxon, 3; O, O-diethyl S-(3,5-dichlorophenyl) phosphorothioate, 4; O-ethyl O-(2-nitro-4-chlorophenyl) methylphosphonate, 5; O, O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate, fenitrothion, 6; O-ethyl S-(3,5-dichlorophenyl) methylphosphonothioate 7) and a carboxylate ester (p-nitrophenyl acetate, 2) catalyzed by methoxide and the Zn2+(-OCH3) complex of 1,5,9- triazacyclododecane (1 : Zn2+(-OCH3)) were studied in methanol and d1-methanol at 25°C. In the case of the methoxide reactions inverse skie's were observed for the series with values ranging from 2 to 1.1, except for 7 where the kD/kH = 0.90 ± 0.02. The inverse kD/kH values are consistent with a direct nucleophilic methoxide attack involving desolvation of the nucleophile with varying extents of resolvation of the TS. With the 1 : Zn 2+(-OCH3) complex all the skie values are kD/kH = 1.0 ± 0.1 except for 7 where the value is 0.79 ± 0.06. Arguments are presented that the fractionation factors associated with complex 1 : Zn2+(-OCH3) are indistinguishable from unity. The skie's for all the complex-catalyzed methanolyses are interpreted as being consistent with an intramolecular nucleophilic attack of the Zn2+-coordinated methoxide within a pre-equilibrium metal : substrate complex. The Royal Society of Chemistry 2005.

Mechanistic studies of la3+- And Zn2+-catalyzed methanolysis of aryl phosphate and phosphorothioate triesters. Development of artificial phosphotriesterase systems

The methanolyses of a series of O,O-diethyl O-aryl phosphates (2,5) and O,O-diethyl S-aryl phosphorothioates (6) promoted by methoxide and two metal ion systems, (La3+)2(-OCH3)2 and 4:Zn2+:-OCH3 (4 = 1,5,9- triazacyclododecane) has been studied in methanol at 25°C. Bronsted plots of the log k2 values vs. sspKa for the phenol leaving groups give βlg values of -0.70. -1.43 and -1.12 for the methanolysis of the phosphates and -0.63, -0.87 and -0.74 for the methanolysis of the phosphorothioates promoted by the methoxide, La 3+ and Zn2+ systems respectively. The kinetic data for the metal-catalyzed reactions are analyzed in terms of a common mechanism where there is extensive cleavage of the P-XAr bond in the rate-limiting transition state. The relevance of these findings to the mechanism of action of the phosphotriesterase enzyme is discussed. The Royal Society of Chemistry 2005.

Process for producing bishalophenyl disulfide

This invention is directed to a process for producing a bishalophenyl disulfide, chracterized by reacting a halothiophenol with an alkali metal hydroxide to obtain an alkali metal halothiophenolate and subsequently converting the halothiophenolate into a disulfide with an oxidizing agent in the presence of a mineral acid. By the process, a bishalophenyl disulfide having a high purity can be industrially produced in high yield.

An increased internal rotational barrier in thiophenol caused by meta substituents

The twofold internal barriers to rotation about the C-S bond in 3,5-diX-thiophenols were determined in solution from long-range spin-spin coupling constants.They are 3.4, 4.85, 5.3, 6.45, and 7.25 +/- 10percent kJ/mol for X = H, CH3, OCH3, F, and Cl, respectively.In 3,5-dichloro-4-hydroxythiophenol, V2 is -0.8 kJ/mol as compared to -1.9 kJ/mol in 4-methoxythiophenol.The para substituent here dominates.The observed barriers are in rough agreement with arguments based on perturbation molecular orbital theory and with MO calculations of changes in the barrier caused by substituents.The computed values appear as nearly pure twofold barriers with very small fourfold components.