934-87-2

Basic information

• Product Name: S-PHENYL THIOACETATE
• Synonyms: THIOACETIC ACID S-PHENYL ESTER;S-PHENYL THIOACETATE;PHENYL THIOACETATE;Acetic acid, thio-, S-phenyl ester;Aceticacid,thio-,S-phenylester;Ethanethioicacid,Sphenylester;Ethanethioicacid,S-phenylester;Phenyl thiolacetate
• CAS NO: 934-87-2
• Molecular Formula: C₈H₈OS
• Molecular Weight: 152.21
• EINECS: 213-294-2
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiol Esters
• Mol File: 934-87-2.mol
• Article Data: 153

Chemical Properties

• Melting Point: 18-19 °C
• Boiling Point: 99-100 °C6 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: Colorless/Liquid
• Density: 1.124 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0434mmHg at 25°C
• Refractive Index: n20/D 1.57(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: S-PHENYL THIOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: S-PHENYL THIOACETATE(934-87-2)
• EPA Substance Registry System: S-PHENYL THIOACETATE(934-87-2)

Safety Data

• RIDADR: UN 3334
• WGK Germany: 2
• RTECS: AJ7559000
• Hazardous Substances Data: 934-87-2(Hazardous Substances Data)

Usage

Uses

S-Phenyl thioacetate was used as a substrate to measure the esterase activity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 2713, 1978 DOI: 10.1021/jo00407a040Tetrahedron Letters, 21, p. 4259, 1980 DOI: 10.1016/S0040-4039(00)92877-6Chemical and Pharmaceutical Bulletin, 30, p. 4242, 1982 DOI: 10.1248/cpb.30.4242

InChI:InChI=1/C8H8OS/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3

Upstream product

• 108-24-7 acetic anhydride 
• 108-98-5 thiophenol 
• 546-67-8 lead(IV) tetraacetate 
• 75-36-5 acetyl chloride 
• 17314-33-9 tributyltin phenyl sulfide 
• 938-81-8 N-nitrosoacetanilide 
• 507-09-5 tiolacetic acid 
• 100-51-6 benzyl alcohol 
• 7417-81-4 benzyl phenyl sulfoxide 
• 17414-02-7 1,2-dimethylprop-1-enyl phenyl sulfide 
• 591-50-4 iodobenzene 
• 115981-46-9 methyl(benzenethiolato){1,2-bis(diphenylphosphino)ethane}palladium 
• 501919-08-0 3-(4-trifluoromethylphenyl)isoxazole 
• 1006-65-1 3-phenylisoxazole 

Downstream Products

• 47510-31-6 S-phenyl decenedithioate 
• 21514-24-9 mercury thiophenolate 
• 40053-29-0 S-phenyl 3-oxobutanethioate 
• 27738-91-6 4,4'-disulfanediyldibenzenesulfonyl chloride 
• 14859-20-2 {[1,1-bis(phenylthio)ethyl]thio}benzene 
• 58058-61-0 3-Hydroxy-3,3-diphenyl-thiopropionic acid S-phenyl ester 
• 17903-06-9 S-Tripropyl-silyl-thiophenol 
• 15780-63-9 γ-thiobutylylacetylacetone 
• 36797-15-6 phenyl dithioacetate 
• 58058-62-1 β-Hydroxycarboxylsaeure 
• 42479-96-9 S-phenyl 3-hydroxy-3-phenylpropanethioate 
• 618-42-8 1-piperidin-1-yl-ethanone 
• 108-98-5 thiophenol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside 

Relevant articles and documents

Organocatalytic enantioselective decarboxylative addition of malonic half thioesters to imines

We describe a biomimetic organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to imines. This simple protocol makes use of readily available Cinchona-derived organocatalysts and nucleophiles at the carboxylate oxidation state. The resulting β-amino thioesters, being attractive precursors for the preparation of optically active, β-amino acids, are formed in good yields and in up to 79 % ee. As suggested by several mechanistic insights the desired products are formed via initial formation of a thioester acetate enolate via decarboxylation of the malonic acid half thioester, followed by addition to the imine.

Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols

Abstract: An unprecedented metal-, halogen- and solvent-free, MSAA-promoted S-carbonylation of thiols with feedstock acids has been developed. This new transformation provides an efficient and atom-economic strategy for the synthesis of thioesters in a single operation from readily available and inexpensive starting materials. The reaction avoids the use of expensive and hazardous coupling reagents, bases and generates water as the only by-product, thus making this chemical synthetic process more viable, environment-friendly and contributing towards sustainable chemistry. Graphic abstract: [Figure not available: see fulltext.].

Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides

An alternative thioesterification reaction via copper-catalyzed oxidative coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivativ