27998-60-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloroethyl phenyl sulphoxide is used as a pharmaceutical intermediate for the synthesis of various medicinal compounds. Its unique structure allows it to be a versatile building block in the creation of new drugs with potential therapeutic applications.
Used in Pesticide Industry:
This chemical has been studied for its potential use as a pesticide, leveraging its chemical properties to control, repel, or kill pests. Its effectiveness in this application is still under investigation.
Used in Organic Synthesis:
As a chemical intermediate, 2-Chloroethyl phenyl sulphoxide is used in the manufacturing process of certain organic compounds. Its reactivity and functional groups make it a valuable precursor in organic synthesis for developing new chemical entities.
Used in Manufacturing of Pharmaceuticals:
2-Chloroethyl phenyl sulphoxide has been utilized in the production of some pharmaceuticals, contributing to the synthesis of active pharmaceutical ingredients or aiding in the formation of drug formulations.

InChI:InChI=1/C8H9ClOS/c9-6-7-11(10)8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 108-98-5 thiophenol 
• 107-06-2 1,2-dichloro-ethane 
• 5535-49-9 2-Chloroethyl phenyl sulfide 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 86428-23-1 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine 

Downstream Products

• 90003-94-4 (2-Jod-ethyl)-phenylsulfoxid 
• 136370-30-4 Phenyl 2-chloro-1-fluoroethyl sulfide 
• 114969-03-8 (1-fluoroethenyl)phenylsulfane dioxide 
• 125927-29-9 2-Chloro-1-fluoroethyl Phenyl Sulfone 
• 125927-34-6 1-Fluoro-1-(phenylsulfonyl)-3-pentanone 
• 125927-35-7 1-Fluoro-1-(phenylsulfonyl)-3-pentanol 
• 125927-32-4 2-<2-Fluoro-2-(phenylsulfonyl)ethyl>-1,3-dioxolane 
• 125927-33-5 2-<2-Fluoro-2-(phenylsulfonyl)ethyl>-1,4-dioxane 
• 75-01-4 chloroethylene 
• 882-33-7 diphenyldisulfane 
• 5535-49-9 2-Chloroethyl phenyl sulfide 
• 87549-08-4 1-(2-phenylsulfinylethyl)-2-benzoylpyrrole 

Relevant academic research and scientific papers

Efficient oxidation of sulfur mustard and its simulants using N-tert-butyl-N-chlorocyanamide

N-tert-Butyl-N-chlorocyanamide reacts with sulfur mustard instantaneously to give a corresponding nontoxic sulfoxide in quantitative yield. The transformation is selective and takes place in semi-aqueous medium (CH 3CN/H2O, 1:1), even at subzero temperatures. Copyright Taylor & Francis Group, LLC.

New microemulsions for oxidative decontamination of mustard gas analogues and polymer-thickened half-mustard

Chemical decontamination of toxic compounds (warfare agents and pesticides) is of increasing importance. In this study, we report the oxidation of mustard gas analogues in microemulsion media. A first formulation, very well-suited for stock-pile destruction, allows a fast, quantitative and chemoselective oxidation of the analogues. In a second formulation, the choice of microemulsion components used allowed us to study the oxidation of a polymer-thickened half-mustard (2-chloroethylphenyl sulfide), opening the field of application of these microemulsions to on-site decontamination. These results confirm both the efficiency and potential of microemulsions for mustard gas destruction/decontamination in essentially aqueous systems.

A simple and efficient chemical decontamination of sulfur mustard (HD) using 1,8-diazabicyclo[5,4,0]undec-7-ene hydrobromide-perbromide

A simple and efficient chemical decontamination method was developed against sulfur mustard (HD), an extremely toxic and persistent chemical warfare agent. The method involves treatment of chemical warfare agent HD and its simulants, i.e., methyl p-tolyl sulfide, 2-chloroethyl phenyl sulfide, and 2-chloroethyl ethyl sulfide, with 1,8-diazabicyclo[5,4,0]undec-7-ene hydrobromide-perbromide at room temperature in 1:3 acetonitrile-water system as well as in aqueous medium. The reagent has efficiency to oxidize sulfur mustard in a controlled manner to form nontoxic sulfoxide avoiding overoxidation to the toxic sulfone. Reaction products of the oxidation were isolated and analyzed by gas chromatography-mass spectrometry and 1H NMR.

Hydrogen peroxide oxidation of mustard-model sulfides catalyzed by iron and manganese tetraarylporphyrines. Oxygen transfer to sulfides versus H2O2 dismutation and catalyst breakdown

Fe(III)- and Mn(III)-meso-tetraarylporphyrin catalysis of H2O2 oxidation of dibenzyl and phenyl-2-chloroethyl sulfides, 1, is investigated in ethanol with the aim of designing catalytic systems for mustard decontamination. The sulfide conversion, the sulfoxide and sulfone yields, the oxygen transfer from H2O2 to the sulfide, and the catalyst stability depend markedly on the metal, on the substituents of its ligand, and on the presence or the absence of a cocatalyst, imidazole or ammonium acetate. With Fe, sulfones, the only oxidation products, are readily obtained whatever the ligand (TPP, F20TPP, or TDCPP) and the cocatalyst; the oxygen transfer is fairly good, up to 95% when the catalyst concentration is small ([1]/[Cat] = 420); the catalyst breakdown is insignificant only in the absence of any cocatalyst. With Mn, the sulfide conversion is achieved completely when the ligand is TDCPP or TSO3PP, but not F20TPP or TPP; a mixture of sulfoxide, 2, and sulfone, 3, is always obtained with [2]/[3] = 3.5-0.85 depending on the ligand and the cocatalyst (electron withdrawing substituents favor 3 and NH4OAc, 2). The catalyst stability is very good, but the oxygen transfer is poor whatever the ligand and the cocatalyst. These results are discussed in terms of a scheme in which sulfide oxygenation, H2O2 dismutation, and oxidative ligand breaking compete. It is shown that the efficiency of the oxygen transfer is related not only to the rate constant of the dismutation route but also to the concentration of the active metal-oxo intermediate, most likely a perferryl or permanganyl species, i.e., to the rate of its formation.

Ti(Phen)(OC2H5)2Cl2: A highly efficient pre-catalyst for selective oxidation of organic sulfides to sulfoxides by hydrogen peroxide

A newly developed and structurally characterized titanium complex [Ti(Phen)(OC2H5)2Cl2] (Phen = 1,10-phenanthroline) is reported as a homogeneous pre-catalyst for the selective oxidation of organic sulfides to sulfoxides with a stoichiometric amount of 30% aq. H2O2 in CH3OH at room temperature. This catalytic system showed high yield (95-100%) and good selectivity (92-100%) during the catalytic reaction in a short period of time.

Divergent electrolysis for the controllable coupling of thiols with 1,2-dichloroethane: A mild approach to sulfide and sulfoxide

Organosulfurs are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that were traditionally synthesized using metal catalysts, oxidants or strong bases, which caused numerous environmental pollution issues. The divergent synthesis of these scaffolds via a single catalysis under catalyst and oxidant free conditions is a fantastic idea to overcome these drawbacks. Here, we report a safe, practical and eco-friendly electrochemical methodology for the controllable dechloro-coupling of 1,2-dichloroethane (DCE) with thiols, providing value-added β-chloroethylsulfurs, which serve as versatile building blocks in the efficient late-stage conversion to bioactive molecules. The mildness and practicality of this protocol was further demonstrated by the total synthesis of anti-gout drug sulfinpyrazone in a 32% total yield over three steps.

Synergistic cooperative effect of CF3SO2Na and bis(2-butoxyethyl)ether towards selective oxygenation of sulfides with molecular oxygen under visible-light irradiation

A safe, practical and eco-friendly method for the switchable synthesis of sulfoxides and sulfones through visible-light-initiated oxygenation of sulfides at ambient temperature under transition-metal-, additives-free and minimal solvent conditions. The synergistic catalytic efforts between CF3SO2Na and 2-butoxyethyl ether represents the key promoting factor for the reaction. This journal is

A safe and compact flow platform for the neutralization of a mustard gas simulant with air and light

A low footprint, mobile, robust and frugal chemical neutralization technology is reported for the oxidative neutralization of a mustard gas simulant. It relies on the inherent properties of a highly engineered continuous flow setup and carefully optimized and simple, yet robust, experimental conditions. The neutralization protocol uses only non-toxic, widely available and cheap chemicals. The continuous flow setup integrates a singlet oxygen generator and exploits its oxidative power to neutralize 2-chloroethyl ethyl sulfide (CEES), the most common thioether mustard gas simulant. The flow reactor can be connected to either pressurized oxygen or air and handles CEES as a 1 M solution in EtOH containing a trace amount (0.06 molpercent) of a non-toxic and widely available photosensitizer (Methylene Blue). Upon irradiation with visible light (orange or white light), total and highly selective neutralization towards the corresponding non-toxic sulfoxide (1-chloro-2-(ethylsulfinyl)ethane, CEESO) is obtained with reactor effluents containing less than 1percent of the corresponding potentially toxic sulfone (1-chloro-2-(ethylsulfonyl)ethane, CEESO2). With a low footprint (L × W × H 94 × 42 × 40 cm), this neutralization technology can be equipped on a vehicle for on-site interventions, localized at a neutralization facility or both. This experimental work is also supported with the computational rationalization of the reactivity of CEES towards singlet oxygen.

Tungstate supported mesoporous silica SBA-15 with imidazolium framework as a hybrid nanocatalyst for selective oxidation of sulfides in the presence of hydrogen peroxide

In this work, a new heterogeneous catalyst (SBA-15/Im/WO4 2?) was prepared, and then its performance in the oxidation of organic sulfides was studied (using 30% H2O2 as green oxidant under neutral reaction conditions). This organic–inorganic hybrid mesoporous material was characterized by various techniques, such as FT-IR, inductively coupled plasma, X-ray powder diffraction, high-resolution-transmission electron microscopy, N2 adsorption–desorption and thermogravimetric analysis. The catalyst was also applied to the selective oxidation of various sulfides. The hybrid catalyst was easily recovered, and was very stable and retained good activity for at least five successive runs without any additional activation. Moreover, there was no remarkable decrease in the activity and selectivity of the catalyst. The products could be easily isolated by just removing the solvent after filtering the catalyst. The yields of the catalytic productions through this catalyst were in the range from 75% to 97%.

Oxidative Neutralization of Mustard-Gas Simulants in an On-Board Flow Device with In-Line NMR Monitoring

The fast and effective neutralization of the mustard-gas simulant 2-chloroethyl ethyl sulfide (CEES) using a simple and portable continuous flow device is reported. Neutralization takes place through a fully selective sulfoxidation by a stable source of hydrogen peroxide (alcoholic solution of urea–H2O2 adduct/MeSO3H freshly prepared). The reaction progress can be monitored with an in-line benchtop NMR spectrometer, allowing a real-time adjustment of reaction conditions. Inherent features of millireactors, that is, perfect control of mixing, heat and reaction time, allowed the neutralization of 25 g of pure CEES within 46 minutes in a 21.5 mL millireactor (tR=3.9 minutes). This device, which relies on affordable and nontoxic reagents, fits into a suitcase, and can be deployed by police/military forces directly on the attack site.