3786-20-7

Basic information

• Product Name: S-phenyl-O-benzyl thiolcarbonate
• Synonyms: S-phenyl-O-benzyl thiolcarbonate
• CAS NO: 3786-20-7
• Molecular Weight: 244.314
• Mol File: 3786-20-7.mol

Chemical Properties

• CAS DataBase Reference: S-phenyl-O-benzyl thiolcarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: S-phenyl-O-benzyl thiolcarbonate(3786-20-7)
• EPA Substance Registry System: S-phenyl-O-benzyl thiolcarbonate(3786-20-7)

Safety Data

• Hazardous Substances Data: 3786-20-7(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 882-33-7 diphenyldisulfane 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 108-98-5 thiophenol 
• 13464-19-2 phenyl chlorothioformate 

Downstream Products

• 5276-81-3 S-benzyl-N-benzyloxycarbonyl-L-thiocysteine S-phenyl ester 
• 2899-57-2 Sphenyl N-benzyloxycarbonylaminoethanothioate 

Relevant articles and documents

Investigations into the carbonic anhydrase inhibition of COS-releasing donor core motifs

Carbonyl sulfide (COS) releasing scaffolds are gaining popularity as hydrogen sulfide (H2S) donors through exploitation of the carbonic anhydrase (CA)-mediated hydrolysis of COS to H2S. The majority of compounds in this emerging class of donors undergo triggerable decomposition (often referred to as self-immolation) to release COS, and a handful of different COS-releasing structures have been reported. One benefit of this donation strategy is that numerous caged COS-containing core motifs are possible and are poised for development into self-immolative COS/H2S donors. Because the intermediate release of COS en route to H2S donation requires CA, it is important that the COS donor motifs do not inhibit CA directly. In this work, we investigate the cytotoxicity and CA inhibition properties of different caged COS donor cores, as well as caged CO2 and CS2 motifs and non-self-immolative control compounds. None of the compounds investigated exhibited significant cytotoxicity or enhanced cell proliferation at concentrations up to 100 μM in A549 cells, but we identified four core structures that function as CA inhibitors, thus providing a roadmap for the future development of self-immolative COS/H2S donor motifs.

Synthesis of thiol esters using nano CuO/Ionic liquid as an eco-friendly reductive system under microwave irradiation

We report an efficient, fast, and environmentally friendly method for the synthesis of a wide range of thiol esters using stable diorganoyl disulfides and acyl chlorides, using CuO nanoparticles and [pmim]Br as the reductive system. This method gave good to excellent isolated yields of the desired products after only three minutes of microwave irradiation. Furthermore, by using the same green approach, we were also able to synthesize thiocarbonates bearing interesting functionalities. We report an efficient, fast, and environmentally friendly method for the synthesis of thiol esters starting from diorganoyl disulfides and acyl chlorides, and using CuO nanoparticles and [pmim]Br as the reductive system. This approach gave good to excellent isolated yields of the desired products in only three minutes under microwave irradiation. Copyright

Zn in ionic liquid: An efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters

A straightforward and efficient methodology is described to synthesize structurally diverse diorganyl selenides, sulfides, seleno- and thioesters by using commercially available Zn dust in ionic liquid. Excellent yields were achieved under neutral conditions at room temperature in a short time. The solvent/ionic liquid is reusable and exhibited higher performance as compared with organic solvents.

Convenient route to thiocarbonates from alcohols, thiols, and triphosgene

An efficient and simple one-pot, three-component procedure has been introduced for the preparation of various thiocarbonates from thiols, alcohols, and triphosgene in dichloromethane. Copyright Taylor & Francis Group, LLC.

Synthesis of S-aryl/alkyl thiolcarbonates from disulfides and chloroformates in the presence of the Zn/AlCl3 system

A simple, general, and high yielding method has been developed for the synthesis of S-aryl/alkyl-O-aryl/alkyl thiolcarbonates from various chloroformates and disulfides by reductive cleavage of the S-S bond with a Zn/AlCl3 system in dry acetonitrile at 80°C.

A new method for synthesis of S-aryl-O-alkyl thiolcarbonates: Selenium-catalyzed reaction of alcohols with carbon monoxide and diaryl disulfides

A unique catalytic ability of selenium has been developed. When alcohols were allowed to react with diaryl disulfides in the presence of a catalytic amount of selenium under a pressurized carbon monoxide, S-aryl-O-alkyl thiolcarbonates were obtained in moderate to good yields.