5535-49-9

Usage

Uses

Used in Chemical Warfare Agent Detection:
2-Chloroethyl phenyl sulfide is used as a target analyte in bioassays for the detection of mustard agent. Its role as a stimulant for sulfur mustard agents makes it a valuable compound in the development of detection methods and countermeasures against chemical warfare agents.
Used in Chemical Research and Development:
As a simulant for chemical warfare agents, 2-chloroethyl phenyl sulfide is utilized in the research and development of new chemical compounds and materials. Its reactivity with various substances, such as vesicular functionalized double-chain surfactant and hydrogen peroxide, allows for the exploration of new chemical reactions and the synthesis of novel products.
Used in the Production of Chemical Compounds:
2-Chloroethyl phenyl sulfide is used as a starting material or intermediate in the production of various chemical compounds. Its unique chemical properties make it a useful building block for the synthesis of new molecules with potential applications in different industries.
Used in the Chemical Industry:
In the chemical industry, 2-chloroethyl phenyl sulfide is used as a reagent or catalyst in various chemical processes. Its ability to react with different substances and form new compounds makes it a valuable asset in the development of new products and technologies.
Used in Environmental and Safety Studies:
2-Chloroethyl phenyl sulfide is employed in environmental and safety studies to understand the potential risks and impacts of chemical warfare agents on the environment and human health. By using 2-CHLOROETHYL PHENYL SULFIDE as a simulant, researchers can gain insights into the behavior, degradation, and detoxification of sulfur mustard and other related chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 4506, 1993 DOI: 10.1021/jo00068a063Synthesis, p. 577, 1978

InChI:InChI=1/C8H9ClS/c9-6-7-10-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 699-12-7 2-(phenylthio)ethanol 
• 100520-02-3 1-butoxy-2-phenylsulfanyl-ethane 
• 16670-48-7 2-chloroethyl benzenesulfonate 
• 108-98-5 thiophenol 
• 141-52-6 sodium ethanolate 
• 107-07-3 2-chloro-ethanol 
• 56-23-5 tetrachloromethane 
• 74-85-1 ethene 
• 931-59-9 benzenesulfenyl chloride 
• 930-69-8 sodium thiophenolate 
• 420-12-2 thirane 
• 62-53-3 aniline 
• 83594-06-3 2-(phenylthio)ethanesulfonyl chloride 
• 75-05-8 acetonitrile 

Downstream Products

• 1209-11-6 1-[2-(phenylthio)ethyl]piperidine 
• 69967-32-4 4-(2-phenylsulfanyl-ethyl)-morpholine; hydrochloride 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 90535-42-5 1-methylsulfanyl-2-phenylsulfanyl-ethane 
• 118768-67-5 2-phenylsulfanyl-ethyl thiocyanate 
• 52162-05-7 2-amino-4-phenylthiobutanoic acid 
• 938-09-0 2-chloroethyl phenyl sulfone 
• 13865-49-1 [2-(phenylsulfanyl)ethyl]benzene 
• 101432-48-8 1,1′-[sulfanediylbis(ethane-2,1-diylsulfanediyl)]dibenzene 
• 1822-73-7 phenylthioethylene 
• 7319-95-1 N,N-dimethyl-2-(phenylthio)ethan-1-amine 
• 67747-34-6 benzyl[2-(phenylsulfanyl)ethyl]amine 
• 79064-79-2 O-Aethyl--methylthiophosphat 
• 27998-60-3 chloroethyl phenyl sulfoxide 

Relevant academic research and scientific papers

Luminogenic and fluorogenic compounds and methods to detect molecules or conditions

A method to detect the presence or amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided.

Electrophilic alkylation of pseudotetrahedral nickel(II) arylthiolate complexes

A kinetic study is reported for reactions of pseudotetrahedral nickel(II) arylthiolate complexes [(TpR,Me)Ni-SAr] (TpR,Me = hydrotris{3-R-5-methyl-1-pyrazolyl}borate, R = Me, Ph, and Ar = C6H5, C6H4-4-Cl, C6H4-4-Me, C6H4-4-OMe, 2,4,6-Me3C6H2, 2,4,6-iPr3C6H2) with organic electrophiles R'X (i.e., MeI, EtI, BzBr) in low-polarity organic solvents (toluene, THF, chloroform, dichloromethane, or 1,2-dichloroethane), yielding a pseudotetrahedral halide complex [(TpR,Me)Ni-X] (X = Cl, Br, I) and the corresponding organosulfide R'SAr. Competitive reactions with halogenated solvents and adventitious air were also examined. Akin to reactions of analogous and biomimetic zinc complexes, a pertinent mechanistic question is the nature of the reactive nucleophile, either an intact thiolate complex or a free arylthiolate resulting from a dissociative pre-equilibrium. The observed kinetics conformed to a second-order rate law, first order with respect to the complex and electrophile, and no intermediate complexes were observed. In the absence of a mechanistically diagnostic rate law, a variety of mechanistic probes were examined, including kinetic effects of varying the metal, solvent, electrophile, and temperature, as well as the 3-pyrazolyl and arylthiolate substituents. Compared to zinc analogues, the effect of Ni-SAr covalency is also of interest herein. The results are broadly interpreted with respect to the disparate mechanistic pathways.

Oxo-rhenium(V) complexes containing heterocyclic ligands as catalysts for the reduction of sulfoxides

This work reports the catalytic activity of a large variety of oxo-rhenium(V) complexes (1 mol-%) containing the ligands 2-(2-hydroxy-5- methylphenyl)benzotriazole (Hhmpbta), 2-(2-hydroxyphenyl)benzothiazole (Hhpbt), 2-(2-hydroxyphenyl)benzoxazole (Hhpbo), and 2-(2-hydroxyphenyl)-1H-benzimidazole (Hhpbi) in the deoxygenation of sulfoxides with silanes or boranes as the reducing agents. In general, all of the complexes are excellent catalysts, although the PhSiH3/[ReOBr2(hmpbta)(PPh3)] and pinacolborane/[ReOBr2(hmpbta)(PPh3)] systems are the most efficient for the reduction of aromatic and aliphatic sulfoxides and tolerate different functional groups. Copyright

Oxo-Rhenium(V) Complexes Containing Heterocyclic Ligands as Catalysts for the Reduction of Sulfoxides

This work reports the catalytic activity of a large variety of oxo-rhenium(V) complexes (1 mol-%) containing the ligands 2-(2-hydroxy-5-methylphenyl)benzotriazole (Hhmpbta), 2-(2-hydroxyphenyl)benzothiazole (Hhpbt), 2-(2-hydroxyphenyl)benzoxazole (Hhpbo), and 2-(2-hydroxyphenyl)-1H-benzimidazole (Hhpbi) in the deoxygenation of sulfoxides with silanes or boranes as the reducing agents. In general, all of the complexes are excellent catalysts, although the PhSiH3/[ReOBr2(hmpbta)(PPh3)] and pinacolborane/[ReOBr2(hmpbta)(PPh3)] systems are the most efficient for the reduction of aromatic and aliphatic sulfoxides and tolerate different functional groups.

Gallium-catalyzed reductive chlorination of carboxylic acids with copper(II) chloride

Described herein is the direct chlorination of carboxylic acids using copper(II) chloride via a gallium(III)-catalyzed reduction in the presence of a hydrosiloxane. During this reductive chlorination, the counteranions of CuCl2 functioned as a chloride source.

Synthesis of a new class of arylsulfonylethylsulfonylmethyloxazolines and thiazolines

A new class of arylsulfonylethylsulfonylmethyl oxazolines and thiazolines were prepared using multistep, one-pot methodologies exploiting lanthanide alkoxides and under microwave irradiation. The microwave method provides an excellent approach in a single step with high yields.

The chemistry of cyclic carbaphosphazenes: The first observation of (R 2PN)(ClCN)2 (R=Cl, Ph) as a reagent for the conversion of alcohols to aldehydes, ketones, and alkyl chlorides

The oxidation of nine primary and secondary alcohols to the corresponding aldehydes and ketones has been carried out under mild conditions and in good yields using the cyclocarbaphosphazenes (R2PN)(ClCN)2 [R2P = Cl2 P(1), Ph2P(2)] along with dimethylsulfoxide. While both the P-Cl and C-Cl bonds of the carbaphosphazene can in principle bring about the reaction, we observed an increased preference for the C-Cl bonds over the P-Cl bonds in the oxidation of alcohol. Blocking the reactive P site on the heterocyclic ring with the phenyl groups was found to reduce the yields of the oxidized products, while blocking the C- sites with diethylamino groups resulted in no reaction. In addition, along with DMF, the same cyclocarbaphosphazene has been found to be useful for the conversion of alcohols to alkyl chlorides. Copyright Taylor & Francis Group, LLC.

A highly efficient carbon-sulfur bond formation reaction via microwave-assisted nucleophilic substitution of thiols to polychloroalkanes without a transition-metal catalyst

An efficient carbon-sulfur bond formation reaction has been developed under microwave irradiation. This reaction affords a novel and rapid synthesis of thioacetals and sulfides under mild conditions. This method is particularly noteworthy given its experimental simplicity and high generality, and no transition-metal catalysts were needed under our conditions.

Deoxygenation of sulfoxide and aza-aromatic N-oxide using a protocol of indium and acyl chloride

Sulfoxides and aza-aromatic N-oxides were deoxygenated using a system of indium and pivaloyl chloride at room temperature to give the corresponding sulfides and aza-aromatics in high yields. Georg Thieme Verlag Stuttgart.

Synthesis and pharmacological properties of benzamide derivatives as selective serotonin 4 receptor agonists

A series of 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamides with a polar substituent group at the 1-position of the piperidine ring was synthesized and evaluated for its effect on gastrointestinal motility. The benzoyl, phenylsulfonyl, and benzylsulfonyl derivatives accelerated gastric emptying and increased the frequency of defecation. One of them, 4-amino-N-[1-[3-(benzylsulfonyl)propyl]piperidin-4-ylmethyl]-5-chloro-2- methoxybenzamide (13a, Y-36912), was a selective 5-HT4 receptor agonist offering potential as a novel prokinetic with reduced side effects derived from 5-HT3- and dopamine D2 receptor-binding affinity. In the oral route of administration, this compound enhanced gastric emptying and defecation in mice, and has a possibility as a prokinetic agent, which is effective on both the upper and the lower gastrointestinal tract.