64050-18-6

Basic information

• Product Name: ethyl (2E)-3-(phenylsulfanyl)prop-2-enoate
• Synonyms: 2-Propenoic acid, 3- (phenylthio)-, ethyl ester; 2-Propenoic acid, 3-(phenylthio)-, ethyl ester; 2-propenoic acid, 3-(phenylthio)-, ethyl ester, (2E)-; 3-(Phenylthio)acrylic acid ethyl ester; Ethyl (2E)-3-(phenylsulfanyl)acrylate
• CAS NO: 64050-18-6
• Molecular Formula: C₁₁H₁₂O₂S
• Molecular Weight: 208.2768
• Mol File: 64050-18-6.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 302°C at 760 mmHg
• Flash Point: 137.5°C
• Density: 1.13g/cm³
• Vapor Pressure: 0.00102mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: ethyl (2E)-3-(phenylsulfanyl)prop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2E)-3-(phenylsulfanyl)prop-2-enoate(64050-18-6)
• EPA Substance Registry System: ethyl (2E)-3-(phenylsulfanyl)prop-2-enoate(64050-18-6)

Safety Data

• Hazardous Substances Data: 64050-18-6(Hazardous Substances Data)

Upstream product

• 5941-55-9 ethyl 3-ethoxyacrylate 
• 108-98-5 thiophenol 
• 116074-63-6 [((E)-Hex-2-enyl)sulfanyl]-benzene 
• 623-47-2 propynoic acid ethyl ester 
• 882-33-7 diphenyldisulfane 
• 140-88-5 ethyl acrylate 
• 31930-36-6 ethyl (Z)-3-iodopropenoate 
• 60805-64-3 ethyl 3-(phenylthio)propionate 
• 105-37-3 Ethyl propionate 
• 3674-13-3 2,3-dibromopropionic acid ethyl ester 
• 31930-36-6 ethyl (E)-3-iodopropenoate 
• 583-60-8 2-Methylcyclohexanone 
• 5459-35-8 2-bromo-acrylic acid ethyl ester 

Downstream Products

• 711-29-5 3-phenylsulfonyl-2(Z)-propenoic acid 

Relevant articles and documents

Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement

A gold(I)-catalyzed enantioselective thioallylation of propiolates with allyl sulfides is described. The key mechanistic element is a sulfonium-induced Claisen rearrangement which helps minimize the allyl dissociation and render higher enantioselectivity. This protocol features remarkable scope of the allyl moiety, allowing enantiocontrolled synthesis of all-carbon quaternary centers, and exhibits exceptional functional group compatibility with many Lewis bases and π-bonds. This intermolecular variant of Claisen rearrangement forges both C-S and C-C bonds concomitantly, providing efficient access to interesting optically active organosulfur compounds which can be transformed further through the vinyl sulfide as a functional handle. The rate of the reaction was zeroth order with respect to allyl sulfides, which suggested a reversible inhibition, providing a resting state for the catalyst. The Hammett plot displayed a correlation with σp values, suggesting a turnover-limiting sigmatropic rearrangement where decreased electron-density on sulfur accelerated the rearrangement.

Air Oxidative Radical Oxysulfurization of Alkynes Leading to α-Thioaldehydes

Air oxidative radical oxysulfurization of alkynes initiated by 0.5 mol % tert-butyl hydroperoxide with arylthiols is described. The reaction proceeded at room temperature in the presence of 5% mol water to afford selective α-thioaldehydes. (Chemical Equation Presented).

A recyclable biphasic system for stereoselective and easily handled hydrochalcogenations

Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, ste