502-55-6

Usage

Uses

Insecticide formulations; herbicide.

InChI:InChI=1/C6H10O5S/c1-3-9-5(7)10-11-6(8)12-4-2/h3-4H2,1-2H3

Upstream product

• 1851-77-0 bis-ethoxythiocarbonyl-trisulfane 
• 1851-71-4 bis(ethoxythiocarbonyl) tetrasulfide 
• 121-02-8 2-methyl-5-nitrobenzene-1-sulfonyl chloride 
• 140-89-6 potassium ethyl xanthogenate 
• 594-42-3 chlorothio-trichloro-methane 
• 28563-38-4 ethylxanthogenate 
• 596-43-0 bromo-triphenyl-methane 
• 600-31-7 2-bromomalonic acid 
• 74144-45-9 benzyl-bromo-malonic acid 
• 506-68-3 bromocyane 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 7553-56-2 iodine 
• 140-90-9 sodium O-ethyl dithiocarbonate 

Downstream Products

• 705-75-9 O-Ethyl N-Cyclohexylthiocarbamate 
• 3111-89-5 O-ethyl-N-phenylthiocarbamate 
• 17435-29-9 -bis-ethylxanthogenat 
• 26416-46-6 (Bis-(4-dimethylamino-phenyl)-methylen)-bis-ethylxanthogenat 
• 2905-52-4 bis(ethoxythiocarbonyl) sulfide 
• 1851-77-0 bis-ethoxythiocarbonyl-trisulfane 
• 17435-01-7 Diphenyl-bisaethoxythiocarbonylmercapto-methan 
• 140-90-9 sodium O-ethyl dithiocarbonate 
• 327989-09-3 C₈H₁₅NOS₄ 
• 151-01-9 O-ethyl hydrogen dithiocarbonate 
• 102-08-9 N,N-diphenylthiourea 
• 302-04-5 Thiocyanate 
• 455939-83-0 C₁₆H₂₁NO₃S₂ 
• 455939-88-5 C₁₈H₃₁NO₂S₂ 

Relevant academic research and scientific papers

Dual roles of a xanthate as a radical source and chain transfer agent in the photoinitiated RAFT polymerization of vinyl acetate

A high level of control over the photoinitiated RAFT polymerization of vinyl acetate (VAc) was achieved using a specifically designed xanthate, S-2-cyano-2-propyl-O-ethyl xanthate (CPEC), which acted as a radical source and a chain transfer agent simultaneously. Unlike other RAFT processes, the present system did not use any additional radical initiator, while achieving greater control over the polymerization than the photoiniferter process. The molecular weight of the resulting polymer could be modulated by changing the initial [VAc]0/[CPEC]0 ratio, but the control over the polymerization was lost with a very low initial [VAc]0/[CPEC] 0 ratio. The intensity of UV irradiation affected the polymerization by reducing the induction period and increasing the rate of polymerization but did not affect the molecular weight of the resulting polymer.

Spectroelectrochemistry of potassium ethylxanthate, bis(ethylxanthato)nickel(II) and tetraethylammonium tris(ethylxanthato)-nickelate(II)

Electrochemical and chemical oxidation of S2COEt-, Ni(S2COEt)2, and [Ni(S2COEt)3]- have been studied by CV and in situ UV-VIS spectroscopy in acetonitrile. Cyclic voltammograms of S2COEt- and Ni(S2COEt)2 display one (0.00 V) and two (0.35 and 0.80 V) irreversible oxidation peaks, respectively, referenced to an Ag/Ag+ (0.10 M) electrode. However, the cyclic voltammogram of [Ni(S2COEt)3]- displays one reversible (-0.15 V) and two irreversible (0.35, 0.80 V) oxidation peaks, referenced to an Ag/Ag+ electrode. The low temperature EPR spectrum of the oxidatively electrolyzed solution of (NEt4)[Ni(S2COEt)3] indicates the presence of [NiIII(S2COEt)3], which disproportionates to Ni(S2COEt)2, and the dimer of the oxidized ethylxanthate ligand, (S2COEt)2 ((S2COEt)2 = C2H5OC(S)SS(S)COC2H5), with a second order rate law. The final products of constant potential electrolysis at the first oxidation peak potentials of S2COEt-, Ni(S2COEt)2, and [Ni(S2COEt)3]- are (S2COEt)2; Ni2+(sol) and (S2COEt)2; and Ni(S2COEt)2 and (S2COEt)2, respectively. The chemical oxidation of S2COEt- to (S2COEt)2, and [Ni(S2COEt)3]- to (S2COEt)2 and Ni(S2COEt)2 were also achieved with iodine. The oxidized ligand in the dimer form can be reduced to S2COEt- with CN- in solution.

Poly(ethylene glycol)-block-poly(N-vinylformamide) copolymers synthesized by the RAFT methodology

The radical polymerization of N-vinylformamide was followed and found to proceed in a controlled manner if an appropriate RAFT agent is employed. Use of a poly(ethylene glycol) macro-RAFT agent allowed for the generation of block copolymers of PEG and PNVF.

Thiol-end-functionalized polyethylenes

Synthesis of well-defined and highly thiol-end-functionalized polyethylene (PE-SH) was performed using olefin polymerization by coordination chemistry and robust functionalization chemistries. Using a Nd-based catalyst in combination with n-butyloctylmagnesium (BOMg), dipolyethylenylmagnesium compounds (PE-Mg-PE) were first prepared by catalyzed polyethylene chain growth on magnesium. Taking advantage of the reactivity of the carbon-magnesium bonds so formed, several functionalization strategies were assessed with the main aim of producing the targeted PE-SH in the simplest and most efficient way. In particular, polysulfurs and thiothiocarbonylated-end-functionalized polyethylenes were successfully obtained and reduced by lithium aluminum hydride (LiAlH 4) to give the desired PE with up to 90% thiol chain end functionality.

Activating ATRP Initiators to Incorporate End-Group Modularity into Photo-RAFT Polymerization

Heterogeneous photocatalysis is increasingly used in reversible deactivation radical polymerization (RDRP). In this study, we found that alkyl bromide redox chemistry typically found in atom transfer radical polymerization (ATRP) can be incorporated in concert with dithiocarbonyl disulfide chemistry into the reversible addition-fragmentation chain transfer (RAFT) process via bismuth oxide photocatalysis. This amalgamation of mechanisms introduces end-group modularity - a new layer of control - into RAFT polymers uniquely enabled by photoredox catalysis. We found that a diversity of functionality can be installed at the α-end group via alkyl bromides, while the molecular weight distribution can be tuned seamlessly at the ω-end group through the simultaneous addition of multiple disulfides.

NH4I/EtOCS2K promoted synthesis of substituted benzils from diphenylacetylene derivatives

A facile protocol is described for the synthesis of benzil derivatives from readily accessible diarylacetylene derivatives using the NH4I/EtOCS2K system. This novel protocol results in excellent chemoselectivity and provided good to excellent yields. A control experiment indicated that the reaction proceeds via NH4I promoted EtOCS2K dimerization to give the corresponding dixanthogen and subsequent dixanthogen assisted oxidation.

Coupling of gem-difluorinated organozinc reagents with S-electrophiles

gem-Difluorinated organozinc reagents, which were prepared by insertion of CF2-fragment into C[sbnd]Zn bond, couple with diethyl dixanthogen, di(benzothiazolyl) disulfide, and tetraethylthiuram disulfide. The reaction is promoted either by a copper(I) catalyst or by irradiation with blue light in the presence of Eosin Y disodium salt.

Photochemistry of S -phenacyl xanthates

Various synthetically readily accessible S-phenacyl xanthates are shown to undergo photoinitiated homolytic scission of the C-S bond in the primary step. The resultant fragments, phenacyl and xanthic acid radicals, recombine to form symmetrical 1,4-diketones and xanthogen disulfides, respectively, in high to moderate chemical yields in chemically inert solvents. They can also be efficiently trapped by a hydrogen-atom-donating solvent to give acetophenone and xanthic acid derivatives. The latter compound is in situ thermally converted to the corresponding alcohol in high chemical yields. S-Phenacyl xanthates could thus be utilized as synthetic precursors to the above-mentioned compounds or as photoremovable protecting groups for alcohols in which the xanthate moiety represents a photolabile linker. The photochemically released phenacyl radical fragments efficiently but reversibly add to the thiocarbonyl group of the parent xanthate molecule. The kinetics of this degenerative reversible addition-fragmentation transfer (RAFT)/macromolecular design via the interchange of xanthates (MADIX) mechanism was studied using laser flash photolysis (LFP) and density functional theory (DFT) calculations. The rate constants of the RAFT addition step, kadd ～ 7 × 108 M-1 s-1, and phenacyl radical addition to a double bond of 1,1-diphenylethylene, kadd ～ 108 M-1 s -1, in acetonitrile were experimentally determined by LFP. In addition, photoinitiation of the methyl methacrylate polymerization by S-phenacyl xanthate is demonstrated. The polydispersity index of the resulting poly(methyl methacrylate) was found to be ～1.4. We conclude that S-phenacyl xanthates can serve simultaneously as photoinitiators as well as RAFT/MADIX agents in polymerization reactions.

A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants

A novel synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate and primary and secondary amines, using three oxidizing systems, has been developed on the laboratory scale, and the method using sodium hypochlorite has been applied on a semi-industrial scale. The effect of the oxidizing agents, sodium hypochlorite, in-situ-generated peracetic acid, and the manganese(II) acetate/oxygen system on product purity and yield was studied. The results obtained by use of these three methods were compared with those obtained by reaction of sodium ethyl xanthogenacetate and amines, and of sodium ethyl xanthate with amines in the presence of sulfated nickel zeolite catalyst. The reaction mechanism of sodium hypochlorite oxidation has been established on the basis of isolation of reaction intermediates and determination of their structure by use of Fourier-transform infrared, 1H and 13C NMR, and mass spectrometric methods. The suggested sodium hypochlorite and manganese(II) acetate/oxygen systems have many advantages in comparison with commercial and catalytically promoted synthetic methods, because they are new ecologically friendly syntheses. Springer-Verlag 2010.

Polymer-protein conjugates from ω-aldehyde endfunctional poly(N-vinylpyrrolidone) synthesised via xanthate-mediated living radical polymerisation

Aldehyde ω-endfunctional poly(N-vinylpyrrolidone) was synthesised via quantitative conversion of a xanthate endfunctional precursor obtained via RAFT-mediated polymerisation. The Royal Society of Chemistry.