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Potassium thioacetate

目录号 : GC25780

Potassium thioacetate is widely used as a sulfur source in the synthesis of sulfur-containing organic compounds. It has been employed for the synthesis of heterocycles, polymers, transition-metal ligands, nanoparticles, bioactive compounds and macromolecular inclusion complexes.

Potassium thioacetate Chemical Structure

Cas No.:10387-40-3

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25mg
¥556.00
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产品描述

Potassium thioacetate is widely used as a sulfur source in the synthesis of sulfur-containing organic compounds. It has been employed for the synthesis of heterocycles, polymers, transition-metal ligands, nanoparticles, bioactive compounds and macromolecular inclusion complexes.

Chemical Properties

Cas No. 10387-40-3 SDF Download SDF
分子式 C2H3KOS 分子量 114.21
溶解度 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 8.7558 mL 43.779 mL 87.558 mL
5 mM 1.7512 mL 8.7558 mL 17.5116 mL
10 mM 0.8756 mL 4.3779 mL 8.7558 mL
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Research Update

Efficient linking of two epoxides using Potassium thioacetate in water and its use in polymerization

Chem Commun (Camb) 2022 Jan 25;58(8):1108-1110.PMID:34979538DOI:10.1039/d1cc06036h.

Here, we show that two epoxides can be efficiently linked using Potassium thioacetate (AcSK) in water even at their imbalanced stoichiometric ratios. We found that the first reaction between epoxide and AcSK gave rise to an intermediate that underwent the second reaction with another epoxide with a reactivity much higher than that of AcSK. Time-dependent 1H NMR measurements revealed that the rate constant of the second reaction was 31 times larger than that of the first reaction. Using this reaction, we succeeded in nonstoichiometric polymerization of a bifunctional epoxide. Furthermore, in the presence of a multifunctional epoxide, we obtained hydrogels and self-standing films. We expect that this straightforward and efficient reaction of versatile reagents, epoxide and AcSK, in water would lead to new applications of epoxides.

Mechanistic Insight into the Cu-Catalyzed C-S Cross-Coupling of Thioacetate with Aryl Halides: A Joint Experimental-Computational Study

J Org Chem 2017 Nov 3;82(21):11464-11473.PMID:28960986DOI:10.1021/acs.joc.7b01991.

The mechanism of the Ullmann-type reaction between Potassium thioacetate (KSAc) and iodobenzene (PhI) catalyzed by CuI associated with 1,10-phenanthroline (phen) as a ligand was explored experimentally and computationally. The study on C-S bond formation was investigated by UV-visible spectrophotometry, cyclic voltammetry, mass spectrometry, and products assessment from radical probes. The results indicate that under experimental conditions the catalytically active species is [Cu(phen)(SAc)] regardless of the copper source. An examination of the aryl halide activation mechanism using radical probes was undertaken. No evidence of the presence of radical species was found during the reaction process, which is consistent with an oxidative addition cross-coupling pathway. The different reaction pathways leading to the experimentally observed reaction products were studied by DFT calculation. The oxidative addition-reductive elimination mechanism via an unstable CuIII intermediate is energetically more feasible than other possible mechanisms such as single electron transfer, halogen atom transfer, and σ-bond methatesis.

CO2 -Promoted Direct Acylation of Amines and Phenols by the Activation of Inert Thioacid Salts

ChemSusChem 2022 May 20;15(10):e202200227.PMID:35289483DOI:10.1002/cssc.202200227.

Herein a carbon dioxide-promoted synthetic approach for the direct amidation between unactivated thioacid salts and amines under mild conditions was developed for a wide range of substrates. The method afforded amides in good to excellent yields under transition-metal-free and activation-reagent-free conditions, in sharp contrast to early methodologies on amide synthesis based on transition-metal catalysis. The method offered a greener and transition metal-free protocol applicable to pharmaceuticals preparations. Phenolic compounds were also found to be suitable acylation substrates with potassium thiosulfide KHS as the only byproduct. Moreover, this approach was applied to amide synthesis of valuable bio-active molecules such as moclobemide, melatonin, and a fungicide. Insights into the reaction mechanism involving carbon dioxide were provided through NMR spectroscopy and computational calculations. A plausible mechanism was proposed that involves weak interactions between carbon dioxide and Potassium thioacetate in a dynamic equilibrium state formation of a six-membered ring.

Copper-catalyzed diastereoselective hydrothioetherification of oxa(aza)benzonorbornadienes

Org Biomol Chem 2020 May 13;18(18):3575-3584.PMID:32347285DOI:10.1039/d0ob00659a.

A novel copper-catalyzed hydrothioetherification of oxa(aza)bicyclic alkenes with Potassium thioacetate and aryl or alkyl iodides to synthesize unsymmetrical thioethers has been developed. Notably, the reaction with complete diastereoselectivity went through a syn-selective addition process to give exo-adducts. In addition, this protocol exhibited high efficiency and good functional group tolerance to afford the target thioethers in moderate to good yields. Based on the results of mechanistic investigations, a plausible mechanism was proposed.

Sulfur-functionalized graphene oxide by epoxide ring-opening

Angew Chem Int Ed Engl 2014 Jul 14;53(29):7613-8.PMID:24895067DOI:10.1002/anie.201404002.

The treatment of graphene oxide (GO) with Potassium thioacetate followed by an aqueous work-up yields a new material via the ring-opening of the epoxide groups. The new material is a thiol-functionalized GO (GO-SH) which is able to undergo further functionalization. Reaction with butyl bromide gives another new material, GO-SBu, which shows significantly enhanced thermal stability compared to both GO and GO-SH. The thiol-functionalized GO material showed a high affinity for gold, as demonstrated by the selective deposition of a high density of gold nanoparticles.