25554-84-1

Basic information

• Product Name: 2-(Ethoxythioxomethylthio)acetic acid
• Synonyms: (Ethoxycarbonothioylthio)acetic acid;[[Ethoxy(thiocarbonyl)]thio]acetic acid;2-(Ethoxythioxomethylthio)acetic acid;Ethyl xanthogeneacetic acid;ETHYLXANTHOGENACETIC ACID;((ethoxycarbothioyl)thio)acetic acid;((Ethoxythiomethyl)thio)acetic acid;2-(ethoxycarbothioylthio)acetic acid
• CAS NO: 25554-84-1
• Molecular Formula: C₅H₈O₃S₂
• Molecular Weight: 180.25
• Mol File: 25554-84-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 311.5°Cat760mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 0.000123mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 2-(Ethoxythioxomethylthio)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Ethoxythioxomethylthio)acetic acid(25554-84-1)
• EPA Substance Registry System: 2-(Ethoxythioxomethylthio)acetic acid(25554-84-1)

Safety Data

• Hazardous Substances Data: 25554-84-1(Hazardous Substances Data)

Usage

Physical state

Clear, colorless liquid

Odor

Strong sulfur-like

Uses

Pesticide intermediate, pharmaceutical production, organic synthesis reagent, organic chemical manufacturing

Health hazards

Corrosive to skin and eyes, respiratory irritation, harmful if ingested or inhaled

Environmental impact

Can cause damage to water sources if released

InChI:InChI=1/C5H8O3S2/c1-2-8-5(9)10-3-4(6)7/h2-3H2,1H3,(H,6,7)

Upstream product

• 140-89-6 potassium ethyl xanthogenate 
• 79-11-8 chloroacetic acid 
• 7732-18-5 water 
• 75-15-0 carbon disulfide 
• 64-17-5 ethanol 
• 79-08-3 bromoacetic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 141-52-6 sodium ethanolate 

Downstream Products

• 6317-17-5 N,N-3-oxapentamethylenethiocarbamoylthioacetic acid 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 936-64-1 morpholinyl thiocarbamate 
• 1925-70-8 5-phenyl-1,3,4-thiadiazole-2(3H)-thione 
• 90438-03-2 (4-sulfamoyl-phenyl)-thiocarbamic acid O-ethyl ester 
• 17996-38-2 N,N-dimethyl ethyl thiocarbamate 
• 3111-89-5 O-ethyl-N-phenylthiocarbamate 
• 861547-85-5 benzhydrylmercaptocarbonylmercapto-acetic acid 
• 817-73-2 ethyl N-methylthiocarbamate 
• 625-57-0 O-ethyl thiocarbamate 
• 26686-32-8 (ethoxycarbonothioyl)-L-phenylalanine 
• 32601-86-8 2-chloro-3-methylquinoxaline 
• 832-66-6 8-methylcaffeine 
• 80907-18-2 2-(4-oxo-2-phenyl-4H-chromen-3-yl)acetic acid 

Relevant articles and documents

One-step double covalent functionalization of reduced graphene oxide with xanthates and peroxides

Radical functionalization of reduced graphene oxide has been achieved by reaction with a xanthate in the presence of peroxide as a radical initiator. X-ray photoelectron spectroscopy, bulk elemental analyses, and thermogravimetric analyses showed that the

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Poly(ε-caprolactone)-block-polysarcosine by Ring-Opening Polymerization of Sarcosine N-Thiocarboxyanhydride: Synthesis and Thermoresponsive Self-Assembly

Biocompatible amphiphilic block copolymers composed of polysarcosine (PSar) and poly(ε-caprolactone) (PCL) were synthesized using ring-opening polymerization of sarcosine N-thiocarboxyanhydride initiated by oxyamine-ended PCL and characterized by NMR, SEC, and DSC. Self-assembling of two triblock copolymers PSar8-b-PCL28-b-PSar8 (CS7) and PSar16-b-PCL40-b-PSar16 (CS10) in dilute solution was studied in detail toward polymersome formation using thin-film hydration and nanoprecipitation techniques. A few giant vesicles were obtained by thin-film hydration from both copolymers and visualized by confocal laser scanning microscope. Unilamellar sheets and nanofibers (with 8-10 nm thickness or diameter) were obtained by nanoprecipitation at room temperature and observed by Cryo-TEM. These lamellae and fibrous structures were transformed into worm-like cylinders and spheres (D 30-100 nm) after heating to 65°C (>Tm,PCL). Heating CS10 suspensions to 90°C led eventually to multilamellar polymersomes (D 100-500 nm). Mechanism II, where micelles expand to vesicles through water diffusion and hydrophilic core forming, was proposed for polymersome formation. A cell viability test confirmed the self-assemblies were not cytotoxic.

Amino acid-based H2S donors:N-thiocarboxyanhydrides that release H2S with innocuous byproducts

A library ofN-thiocarboxyanhydrides (NTAs) derived from natural amino acids with benign byproducts and controlled H2S-release kinetics is reported. Minimal acutein vitrotoxicity was observed in multiple cell lines, while longer-term toxicity in cancer cells was observed, with slow-releasing donors exhibiting the greatest cytotoxic effects.

Inexpensive Radical Methylation and Related Alkylations of Heteroarenes

A simple method for the introduction of a methyl and higher aliphatic group to various heteroarenes using very inexpensive reagents is described. It is based on the radical addition of a carboxylic xanthate followed by decarboxylation. Depending on the heteroarene structure, the decarboxylation can be spontaneous or induced by heating in N,N-dimethylacetamide or N-methyl pyrrolidone in a microwave oven.