137583-58-5

Basic information

• Product Name: ethyl 2-[(2-chlorophenyl)sulfanyl]acetate
• Synonyms: ethyl 2-[(2-chlorophenyl)sulfanyl]acetate
• CAS NO: 137583-58-5
• Molecular Formula: C₁₀H₁₁ClO₂S
• Molecular Weight: 230.71114
• Mol File: 137583-58-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 2-[(2-chlorophenyl)sulfanyl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-[(2-chlorophenyl)sulfanyl]acetate(137583-58-5)
• EPA Substance Registry System: ethyl 2-[(2-chlorophenyl)sulfanyl]acetate(137583-58-5)

Safety Data

• Hazardous Substances Data: 137583-58-5(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 6320-03-2 2-chlorothiphenol 
• 105-36-2 ethyl bromoacetate 
• 34560-82-2 o-chlorophenyl isopropyl sulfide 
• 64-17-5 ethanol 
• 18619-18-6 (2-chloro-phenylsulfanyl)-acetic acid 

Downstream Products

• 18527-20-3 2-[(2-chlorophenyl)sulfanyl]acetonitrile 
• 101080-59-5 2-Chlorphenyl-mercapto-acetamid 
• 145835-22-9 (2-Chloro-benzenesulfinyl)-acetic acid ethyl ester 

Relevant articles and documents

Rhodium-Catalyzed Rearrangement of S/Se-Ylides for the Synthesis of Substituted Vinylogous Carbonates

An efficient rhodium-catalyzed unprecedented oxa-[2,3]-sigmatropic rearrangement of sulfur ylide derived from α-thioesters/ketones and diazo carbonyl compounds has been accomplished for the synthesis of various sulfur-tethered vinylogous carbonates in good to excellent yields. Important features of the developed reaction include wide functional group tolerance, excellent chemo- and regioselectivity, and efficient rearrangement involving the carbonyl motif. The present reaction also equally works well with α-selenoesters for the synthesis of seleno-containing vinylogous carbonates.

Rhodium-catalyzed Sommelet-Hauser type rearrangement of α-diazoimines: Synthesis of functionalized enamides

An efficient rhodium catalyzed Sommelet-Hauser type rearrangement of sulfur ylides derived from α-thioesters and N-sulfonyl-1,2,3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2,3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N-sulfonyl-1,2,3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.

Sulfonium ylide formation and subsequent C[sbnd]S bond cleavage of aromatic isopropyl sulfide catalyzed by hemin in aqueous solvent

Heme is an abundant and widely existed cofactor for a variety of metalloenzymes, whose broader use is generally impeded by its high instability and poor solubility. Here we report an environment-benign and efficient strategy for the sulfonium ylide formation and subsequent C[sbnd]S bond cleavage of aromatic isopropyl sulfides, which was catalyzed by hemin in assistance of Triton X-100. This aqueous catalytic system exhibited good functional group tolerance to a variety of sulfides and diazo esters. And the reaction mechanism was preliminarily proposed on the basis of designed reactions. Furthermore, the cleavage of C[sbnd]S bond followed by introducing a functional ester group to aromatic sulfides, may potentially be employed for the late stage functionalization (LSF) of organosulfur drug in the future.