25554-84-1

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

Downstream Products

• 1925-70-8 5-phenyl-1,3,4-thiadiazole-2(3H)-thione 
• 17996-38-2 N,N-dimethyl ethyl thiocarbamate 
• 817-73-2 ethyl N-methylthiocarbamate 
• 60576-73-0 N'-(2-phenyl-acetimidoyl)-hydrazinecarbothioic acid O-ethyl ester 
• 60576-71-8 N'-benzimidoyl-hydrazinecarbothioic acid O-ethyl ester 
• 625-57-0 O-ethyl thiocarbamate 
• 4468-82-0 O-ethyl hydrazinothioformate 
• 64-17-5 ethanol 
• 7783-06-4 hydrogen sulfide 
• 68-11-1 mercaptoacetic acid 
• 15719-64-9 methylammonium carbonate 
• 1428628-77-6 perfluorophenyl 2-((ethoxycarbonothioyl)thio)acetate 
• 7464-68-8 1,5-dimethyl-4-nitro-1H-imidazole 
• 20041-97-8 2-(1-methyl-4-nitro-1H-imidazol-5-yl)acetic acid 

Relevant academic research and scientific papers

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

Therapeutic Delivery of H2S via COS: Small Molecule and Polymeric Donors with Benign Byproducts

Carbonyl sulfide (COS) is a gas that may play important roles in mammalian and bacterial biology, but its study is limited by a lack of suitable donor molecules. We report here the use of N-thiocarboxyanhydrides (NTAs) as COS donors that release the gas in a sustained manner under biologically relevant conditions with innocuous peptide byproducts. Carbonic anhydrase converts COS into H2S, allowing NTAs to serve as either COS or H2S donors, depending on the availability of the enzyme. Analysis of the pseudo-first-order H2S release rate under biologically relevant conditions revealed a release half-life of 75 min for the small molecule NTA under investigation. A polynorbornene bearing pendant NTAs made by ring-opening metathesis polymerization was also synthesized to generate a polymeric COS/H2S donor. A half-life of 280 min was measured for the polymeric donor. Endothelial cell proliferation studies revealed an enhanced rate of proliferation for cells treated with the NTA over untreated controls.

Controlled polymerization of N-substituted glycine N-thiocarboxyanhydrides initiated by rare earth borohydrides toward hydrophilic and hydrophobic polypeptoids

N-substituted glycine N-thiocarboxyanhydrides (NTAs) are alternative monomers to prepare polypeptoids with large-scale producing potential compared to the corresponding N-carboxyanhydrides (NCAs) due to their easily synthetic approach and stability during

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.

Main-Chain Fluoropolymers with Alternating Sequence Control via Light-Driven Reversible-Deactivation Copolymerization in Batch and Flow

Polymers with regulated alternating structures are attractive in practical applications, particularly for main-chain fluoropolymers. We for the first time enabled controlled fluoropolymer synthesis with alternating sequence regulation using a novel fluorinated xanthate agent via a light-driven process, which achieved on-demand copolymerization of chlorotrifluoroethylene and vinyl esters/amides under both batch and flow conditions at ambient pressure. This method creates a facile access to fluoropolymers with a broad fraction range of alternating units, low dispersities and high chain-end fidelity. Moreover, a two-step photo-flow platform was established to streamline the in-situ chain-extension toward unprecedented block copolymers continuously from fluoroethylene. Influences of structural control were illustrated with thermal and surface properties. We anticipate that this work will promote advanced material engineering with customized fluoropolymers.

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.

Mucus-responsive functionalized emulsions: Design, synthesis and study of novel branched polymers as functional emulsifiers

Mucus lines the moist cavities throughout the body, acting as barrier by protecting the underlying cells against the external environment, but it also hinders the permeation of drugs and drug delivery systems. As the rate of diffusion is low, the development of a system which could increase retention time at the mucosal surface would prove beneficial. Here, we have designed a range of branched copolymers to act as functional mucus-responsive oil-in-water emulsifiers comprising the hydrophilic monomer oligo(ethylene glycol) methacrylate and a hydrophobic dodecyl initiator. The study aimed to investigate the importance of chain end functionality on successful emulsion formation, by systematically replacing a fraction of the hydrophobic chain ends with a secondary poly(ethylene glycol) based hydrophilic initiator in a mixed-initiation strategy; a decrease of up to 75 mole percent of hydrophobic chain ends within the branched polymer emulsifiers was shown to maintain comparative emulsion stability. These redundant chain ends allowed for functionality to be incorporated into the polymers via a xanthate based initiator containing a masked thiol group; thiol groups are known to have mucoadhesive character, due to their ability to form disulfide bonds with the cysteine rich areas of mucus. The mucoadhesive nature of emulsions stabilised by thiol-containing branched copolymers was compared to non-functional emulsions in the presence of a biosimilar mucosal substrate and enhanced adherence to the mucosal surface was observed. Importantly, droplet rupture and mucus triggered release of dye-containing oil was seen from previously highly-stable thiol-functional emulsions; this observation was not mirrored by non-functional emulsions where droplet integrity was maintained even in the presence of mucus.

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.

BRANCHED POLYMERS

The present invention relates to a branched amphiphilic polymer, suitable for stabilizing an emulsion, comprising a plurality of polymer chains comprising hydrophobic chain ends; a plurality of polymer chains comprising functional chain ends capable of associating to a biological substrate; and a plurality of branching units. The present invention also relates to pharmaceutical compositions containing said branched amphiphilic polymers, their methods of use, and methods for their preparation.

POLYDENDRONS

A method of preparing a non-gelled branched vinyl polymer scaffold carrying dendrons, comprising the living or controlled polymerization of a monofunctional vinyl monomer and a difunctional vinyl monomer, using a dendron initiator and at least one further initiator.