622-38-8

Basic information

• Product Name: ETHYL PHENYL SULFIDE
• Synonyms: Benzene,(ethylthio)-;Sulfide, ethyl phenyl;sulfide,ethylphenyl;Thiophenetole;Ethylphenylsulfide,97%;diphenethylsulfane;ethyl(phenyl)sulfane;Ethyl phenyl sulfide 97%
• CAS NO: 622-38-8
• Molecular Formula: C₈H₁₀S
• Molecular Weight: 138.23
• EINECS: 210-731-9
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 622-38-8.mol
• Article Data: 122

Chemical Properties

• Melting Point: -35.21 °C
• Boiling Point: 204-205 °C(lit.)
• Flash Point: 165 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.021 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.566(lit.)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• BRN: 1905731
• CAS DataBase Reference: ETHYL PHENYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL PHENYL SULFIDE(622-38-8)
• EPA Substance Registry System: ETHYL PHENYL SULFIDE(622-38-8)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 13
• HazardClass: TOXIC, STENCH
• Hazardous Substances Data: 622-38-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Ethyl Phenyl Sulfide is used as a reactant for the synthesis of polyoxometalates for layered double hydroxides. It plays a crucial role in the formation of these complex chemical structures, which have various applications in catalysis, energy storage, and environmental remediation.
Used in Preparation of Immobilized Manganese Porphyrin:
Ethyl Phenyl Sulfide is also utilized in the preparation of immobilized manganese porphyrin on functionalized magnetic nanoparticles. This application is significant in the field of biochemistry and materials science, as it allows for the development of novel catalysts and sensors with enhanced properties and performance.
Used in the Study of Activation Parameters:
The chemical properties of Ethyl Phenyl Sulfide make it an interesting subject for research. It has been used in the study of activation parameters involved in its oxidation in tert-butyl alcohol. This research contributes to the understanding of the reaction mechanisms and can potentially lead to the development of more efficient chemical processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 5052, 1980 DOI: 10.1021/jo01313a008Synthetic Communications, 17, p. 703, 1987 DOI: 10.1080/00397918708075744

Upstream product

• 46185-83-5 2-ethoxyquinoline 
• 108-98-5 thiophenol 
• 74-96-4 ethyl bromide 
• 930-69-8 sodium thiophenolate 
• 75-03-6 ethyl iodide 
• 62-53-3 aniline 
• 1496-75-9 Ethanesulfenyl chloride 
• 71-43-2 benzene 
• 75-15-0 carbon disulfide 
• 141-78-6 ethyl acetate 
• 622-63-9 ethyl p-tolyl sulfide 
• 105-58-8 Diethyl carbonate 
• 1822-73-7 phenylthioethylene 
• 3111-52-2 potassium thiophenolate 

Downstream Products

• 21101-79-1 2-ethylsulfanylbenzoic acid 
• 65-85-0 benzoic acid 
• 875241-90-0 4,4'-bis-ethylsulfanyl-benzophenone 
• 3585-73-7 1-[4-(ethylsulfanyl)phenyl]ethan-1-one 
• 22183-04-6 Di-(p-ethylmercapto-phenyl)-methan 
• 116671-43-3 2-Phenylsulfanyl-heptan-4-one 
• 3019-20-3 isopropylthiobenzene 
• 3695-36-1 2-(ethylsulfanyl)-1-methylbenzene 
• 15560-98-2 2-methyl-1-<(1-methylethyl)thio>benzene 
• 100569-75-3 ethylmethylphenylsulfonium perchlorate 
• 52126-73-5 C₁₇H₁₇Cl₃OS 
• 77876-27-8 ethyl-pentachlorophenyl sulfide 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 51207-25-1 ethylphenylsulfoxide 

Relevant articles and documents

Radical Ion Probes. 7. Behavior of a "Hypersensitive" Probe for Single Electron Transfer in Reactions Not Involving Electron Transfer

1-Methyl-5,7-di-tert-butylspiro[2.5]octa-4,7-dien-6-one (8) and 1,1-dimethyl-5,7-di-tert-butylspiro-[2.5]octa-4,7-dien-6-one (1) react with thiophenoxide ion to produce cyclopropane ring-opened products. Thermodynamic considerations effectively rule out any possibility that single electron transfer is involved in theses reactions; the process PhS- + substrate → PhS. + substrate.- is endothermic by over 50 kcal/moll Nucleophilic attack occurs both at the least- and most-hindered carbons of the cyclopropyl group, and the product ratio (R(1°/2°) from 8 and A(1°/3°) from 1, where 1°, 2°, and 3° refer to the regioisomeric phenyl sulfides formed from these substrates) is found to vary with solvent. In dipolar, aprotic solvents, nucleophilic attack occurs preferentially at the least-hindered carbon of the cyclopropyl group (A(1°/2°) and A(1°/3°) ≈ 4-5), consistent with an SN2 mechanism. In protic solvents, products arising from nucleophilic attack at the more-substituted carbon of the cyclopropyl group become increasingly important, consistent with the onset of a carbocationic (SN2(C+)) pathway. The strengths and weaknesses of 1 and 8 as probes for single electron transfer are discussed in the context of these results.

Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction

The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur–sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.

Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage

Aryl thioesters are synthesized via nickel-catalyzed carbonylation of thioacetates with aryl iodides. Alkyl thioacetates undergo coupling with carbon monoxide and aryl iodides to produce the desired aryl thioesters in moderate yields. This catalytic carbonylative coupling process provides a cost-effective and direct approach for the preparation of useful thioesters.

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent

A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.

Palladium complex containing meta-position carborane triazole ligand and preparation method and application of palladium complex

The invention relates to a palladium complex containing a meta-position carborane triazole ligand and a preparation method and application of the palladium complex. The palladium complex is prepared by the following steps: (1) dropwise adding an n-BuLi solution into a meta-position carborane m-C2B10H12 solution, carrying out stirring and reacting, then adding 3-propargyl bromide for a reaction again, and after the reaction is finished, carrying out separating to obtain 1,3-dipropargyl meta-carborane; and (2) under the catalytic condition of a catalyst CuI, carrying out a reaction on 1,3-dipropargyl meta-carborane and aryl azide, then adding PdCl2 into a reaction system, continuing the reaction, and after the reaction is finished, carrying out separation to obtain the palladium complex containing the meta-carborane triazole ligand. Compared with the prior art, the preparation method provided by the invention is simple and green; the complex can efficiently catalyze a coupling reaction of mercaptan and halogenated hydrocarbon to synthesize thioether compounds; reaction conditions are mild, substrate universality is good, catalytic efficiency is high, and few byproducts are produced;and the catalyst has high stability and is not sensitive to air and water.

Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile

An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).

Discovery and application of methionine sulfoxide reductase B for preparation of (S)-sulfoxides through kinetic resolution

Here we report a methionine sulfoxide reductase B (MsrB) enzymatic system for the preparation of (S)-sulfoxides through kinetic resolution of racemic (rac) sulfoxides. Eight MsrB homologue recombinant proteins were expressed and their activities on asymmetric reduction of rac-sulfoxides were analyzed. Among these MsrB homologue proteins, one protein from Acidovorax species showed good activity and enantioselectivity towards several aryl-alkyl sulfoxides. The (S)-sulfoxides were prepared with 93–98% enantiomeric excess through kinetic resolution at initial substrate concentration up to 50 mM. The establishment of MsrB catalytic kinetic resolution system provides a new efficient green strategy for preparation of (S)-sulfoxides.

Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation

A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.

Corey-Chaykovsky Cyclopropanation of Nitronaphthalenes: Access to Benzonorcaradienes and Related Systems

Nitronaphthalene derivatives react as Michael acceptors in the Corey-Chaykovsky reaction with alkyl phenyl selenones and alkyl diphenyl sulfonium salts. Mechanistic studies reveal that sterically demanding substituents at the carbanionic center favor formation of cyclopropanes and suppress competitive β-elimination to the alkylated products. The transformation, demonstrated also on heterocyclic nitroquinoline and nitroindazolines, is an example of transition metal-free dearomatization method.

Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.