methyl (E)-3-phenyl-2-phenylthiopropenoate

Base Information

• Chemical Name: methyl (E)-3-phenyl-2-phenylthiopropenoate
• CAS No.: 58808-71-2
• Molecular Formula: C₁₆H₁₄O₂S
• Molecular Weight: 270.352
• Mol file: 58808-71-2.mol

Synonyms:methyl (E)-3-phenyl-2-phenylthiopropenoate

Chemical Property of methyl (E)-3-phenyl-2-phenylthiopropenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-3-phenyl-2-phenylthiopropenoate

There total 6 articles about methyl (E)-3-phenyl-2-phenylthiopropenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl 2-bromo-3-phenylacrylate (24127-62-6,21788-35-2,21788-36-3) + thiophenol (108-98-5) → methyl (Z)-3-phenyl-2-(phenylsulfanyl)prop-2-enoate (58808-66-5) + methyl (E)-3-phenyl-2-phenylthiopropenoate (58808-71-2) + diphenyldisulfane (882-33-7)

Guidance literature:

With potassium carbonate; In acetone; at 45 ℃; for 18h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

methyl 2-bromo-3-phenylacrylate (24127-62-6,21788-35-2,21788-36-3) + thiophenol (108-98-5) → methyl (Z)-3-phenyl-2-(phenylsulfanyl)prop-2-enoate (58808-66-5) + methyl (E)-3-phenyl-2-phenylthiopropenoate (58808-71-2) + diphenyldisulfane (882-33-7) + methyl 3-phenyl-2,3-diphenylthiopropanoate

Guidance literature:

With potassium carbonate; In acetone; at 45 ℃; for 0.25h; Mechanism; Product distribution;

Reference yield:

phenylpropynoic acid methyl ester (4891-38-7) + diphenyldisulfane (882-33-7) → methyl (Z)-3-phenyl-2-(phenylsulfanyl)prop-2-enoate (58808-66-5) + methyl (E)-3-phenyl-2-phenylthiopropenoate (58808-71-2)

Guidance literature:

diphenyldisulfane; With hydrogenchloride; zinc; In diethyl ether; water; Green chemistry;

phenylpropynoic acid methyl ester; In diethyl ether; water; at 20 ℃; for 1h; Overall yield = 43 %; Overall yield = 0.116 g; stereoselective reaction; Green chemistry;

DOI:10.1002/ejoc.201402668

upstream raw materials:

Methyl cinnamate

benzenesulfenyl chloride

methyl 2-bromo-3-phenylacrylate

thiophenol

Refernces

• 1、 Zhdankin, Viktor V.,Maydanovych, Olena,Herschbach, Jon,Bruno, Jessica,Matveeva, Elena D.,Zefirov, Nikolai S.. "Preparation, structure, and chemistry of phosphorane-derived phenyliodonium sulfonates". . p. 2359 - 2361. Retrieved 2007/10/03.
• 2、 Rosnati, Vittorio,Saba, Antonio,Salimbeni, Aldo,Vettori, Umberto. "THE AdNSNE MECHANISM IN THE REACTION OF PHENOL AND BENZENETHIOL WITH α-BROMO MICHAEL ACCEPTORS IN THE K2CO3-ACETONE SYSTEM". . p. 249 - 256. Retrieved 2007/10/02.