Potassium thioacetate

Manufactured by Merck Group

Sourced in Germany, Switzerland, United Kingdom

Potassium thioacetate is a laboratory chemical used as a precursor in organic synthesis. It is a white, crystalline solid with the molecular formula CH3COSH·K. The compound serves as a source of the acetyl group (-COCH3) and the thiolate group (-S-) in chemical reactions.

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Lab products found in correlation

9 protocols using potassium thioacetate

Synthesis and Characterization of β-Cyclodextrin Derivatives

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β-Cyclodextrin (β-CD, 95%) was purchased from abcr Gmbh (Karlsruhe, Germany); toluene-4-sulfonyl chloride (≥99%), potassium thioacetate (98%), sodium hydroxide (100%), acetonitrile (>99.9%), acetic acid (>99.8%), D₂O (99.9 atom% D) and DMSO-d₆ (99.96 atom% D), 2-propanol (>99.8%), L-arginine (Ar, ≥98.5%), N,N′-methylene-bis-acrylamide (M, 99%), 2,6-di-tert-butyl-p-cresol (98%) and hydrochloric acid (HCl, 37% w/w) were supplied by Sigma–Aldrich (Milano, Italy) and used as received. Lithium hydroxide monohydrate (≥98%), amberlite IRC-86 (H⁺-form; 20–50 mesh), N,N-dimethylformamide (DMF) (99.8%) were purchased from Fluka (Milano, Italy). Acetone ExpertQ^® ACS, ISO, Reag. Ph. Eur. was purchased from Scharlau (Barcelona, Spain).
De-oxygenated water and 2-propanol were obtained by purging nitrogen for 10 min.

Treccani S., Alongi J., Manfredi A., Ferruti P., Cavalli R., Raffaini G, & Ranucci E. (2022). L-Arginine-Derived Polyamidoamine Oligomers Bearing at Both Ends β-Cyclodextrin Units as pH-Sensitive Curcumin Carriers. Polymers, 14(15), 3193.

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Synthesis of Functionalized Thiol Ligands

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1-propanethiol (99%), 3-mercaptopropionic acid (99%), 1-hexanethiol (95%), 1-dodecanethiol (98%), 11-bromoundecanoic acid (95%), triphenylphosphine (99%), N¹,N¹-dimethyl-1,3-propanediamine (99%), 4-(N,N-dimethylamino) pyridine (99%), triethylamine (Et₃N), N,N’-dicyclohexylcarbodiimide (DCC), poly(ethylene glycol) (average MW = 600), poly(ethylene glycol) methyl ether (average MW = 750), sodium borohydride (99.99%, granular), tetrachloroauric acid trihydrate (99.9%) and potassium thioacetate (98%) were purchased from Sigma Aldrich (St. Louis, MO). Silver nitrate (99.9%), 1,3-propanesultone (99%) and 1,1’-carbonyldiimidazole (CDI) (97%) were purchased from Alfa-Aesar (Wardhill, MA). The solvents used in this study (ethanol, dimethyl formamide, chloroform, ethyl acetate, etc.) were also purchased from Sigma-Aldrich and used as purchased. Column purification chromatography of the synthesized ligands was performed using silica gel (60 Å, 230–400 mesh, from Bodman Industries, Aston, PA).

Mishra D., Wang S., Jin Z., Xin Y., Lochner E, & Mattoussi H. (2019). Highly Fluorescent Hybrid Au/Ag Nanoclusters Stabilized with Poly(ethylene glycol)- and Zwitterion-Modified Thiolate Ligands. Physical chemistry chemical physics : PCCP, 21(38), 21317-21328.

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Synthesis and Characterization of Cholinesterase Inhibitors

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Solvents used were purchased from Fisher Scientific (https://www.fishersci.ca) or VWR International (https://ca.vwr.com). Acetylcholine iodide (AChI), acetylthiocholine iodide (ATChI), butyrylcholine iodide (BChI), butyrylthiocholine iodide (BTChI), purified recombinant human AChE, 3,3′- diaminobenzidine tetrahydrochloride (DAB), 1-methylpiperidin-4-ol, (S)-1-methylpyrrolidin-3-ol, (R)-1-methylpyrrolidin-3-ol, 4-iodobenzoyl chloride, 4-fluorobenzoyl chloride, acetyl chloride, butyryl chloride, iodomethane, 2-(dimethylamino)ethanethiol hydrochloride, potassium thioacetate, oxalic acid, gelatine, sodium azide, 1,5-Bis(4-allyldimethylammoniumphenyl)pentan-3-one-dibromide (BW 284c51), and deuterated solvents were purchased from Sigma-Aldrich (https://www.sigmaaldrich.com) or Oakwood Chemical (https://oakwoodchemical.com). BChE purified from human plasma was a gift from Dr. Oksana Lockridge (Eppley Institute, University of Nebraska Medical Centre, Omaha, Nebraska, United States). Gaseous argon (99.999% purity) was purchased from Air Liquide (https://www.airliquide.ca). Ortho-nitrofluoroacetanilide (o-NTFNAC) was synthesised as previously described⁵⁴ (link).

Darvesh S., Banfield S., Dufour M., Forrestall K.L., Maillet H., Reid G.A., Sands D, & Pottie I.R. (2023). A method for the efficient evaluation of substrate-based cholinesterase imaging probes for Alzheimer’s disease. Journal of Enzyme Inhibition and Medicinal Chemistry, 38(1), 2225797.

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Synthesis of Organometallic Compounds

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All reagents were purchased from Acros Organics or Sigma-Aldrich and used without further purification: hexachloroplatinic(IV) acid (H₂PtCl₆·6H₂O, 99%, metals basis), silver nitrate (AgNO₃, 99% metals basis), adamantane-1-thiol (C₁₀H₁₅SH, 95%), cyclohexyl mercaptan (HS-c-C₆H₁₁, 95%), 2-bromoadamantane (C₁₀H₁₅Br, 99.9%), sodium borohydride (NaBH₄, 99.9%), sodium borodeuteride (NaBD₄, 99.5%), potassium thioacetate (C₂H₃KOS, 99.9%), cesium acetate (CH₃COOCs, 99% metals basis), methylene chloride [CH₂Cl₂, high-performance liquid chromatography (HPLC), Sigma-Aldrich], methanol (CH₃OH, HPLC, Sigma-Aldrich), methanol-OD (CH₃OD, 99.5 atom% D, Sigma-Aldrich), water-D2 (D₂O, 99.9 atom% D, Sigma-Aldrich), water-¹⁸O (H₂¹⁸O, 98 atom% ¹⁸O, Sigma-Aldrich), ethanol (CH₃CH₂OH, HPLC, Sigma-Aldrich), ether (C₂H₅OC₂H₅, HPLC, Sigma-Aldrich), N,N-dimethylformamide (C₃H₇NO, HPLC, Sigma-Aldrich), and n-hexane (C₆H₁₄, HPLC, Sigma-Aldrich).

Kang X., Xu F., Wei X., Wang S, & Zhu M. (2019). Valence self-regulation of sulfur in nanoclusters. Science Advances, 5(11), eaax7863.

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Synthesis of Disulfide-Modified Indole Compounds

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Gramine, methyl
iodide, potassium thioacetate, and potassium carbonate were purchased
from Sigma-Aldrich. A total of 1.2 mmol of Gramine was reacted with
an excess of methyl iodide (5 mmol) in 5 mL of 1:5 methanol:acetonitrile
and stirred for 3 h. The precipitate was collected by vacuum filtration
and rinsed with acetone. The resulting solid was then reacted with
an excess of potassium thioacetate (3.6 mmol) in a 5 mL 2:2:1 mixture
of tetrahydrofuran:acetonitrile:water. The mixture was stirred vigorously
for 4 h. A total of 2 mL of water and chloroform were added and the
organic layer was extracted and washed with water. The resulting organic
layer was dried by nitrogen. The product was redissolved in methanol
(4 mL) and an excess of potassium carbonate was added and the mixture
was stirred vigorously for 2 h. The final product identity was confirmed
by MS/MS. Disulfide modifications of indole-3-methanethiol and 1H-indole-3-thiol (purchased from Sigma) were performed in
the same fashion as peptide modifications.

Hendricks N.G., Lareau N.M., Stow S.M., McLean J.A, & Julian R.R. (2014). Bond-Specific Dissociation Following Excitation Energy Transfer for Distance Constraint Determination in the Gas Phase. Journal of the American Chemical Society, 136(38), 13363-13370.

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Synthesis of Functional Polymers via Click Chemistry

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1,3-Bis(isocyanatomethyl)cyclohexane, 1,3-bis(2-isocyanatopropan-2-yl)benzene, 4,4-methylenebis(cyclohexyl isocyanate), 4,4′-methylenebis(phenyl isocyanate), bis(4-hydroxyphenyl)methane, 6-chloro-1-hexanol, 8-chloro-1-octanol, dibutyltin dilaurate sodium azide, 1,1,1-tris(hydroxymethyl)propane, tris-1,3,5-bromomethylbenzene, phloro-glucinol, propargyl alcohol, propargyl bromide, allyl bromide, sodium hydride (NaH), sodium sulfate (Na₂SO₄), potassium thioacetate, diethyl azodicarboxylate (DEAD), tetrabutylammonium iodide, N,N,′,N′,N″ -pentamethyldiethylenetriamine (PMDETA), copper(II) chloride, 2,2-dimethoxy-2-phenylacetophenone (DMPA), triphenyl-phosphine (TPP), tetrahydrofuran (THF), dimethylformamide (DMF), and dimethyl sulfoxide (DMSO) were all purchased from Sigma-Aldrich and used without further purification. Potassium carbonate (K₂CO₃) and hydrochloric acid (HCl) were purchased from Fisher Scientific and used without further purification.

Baranek A., Song H.B., McBride M., Finnegan P, & Bowman C.N. (2016). Thermomechanical Formation–Structure–Property Relationships in Photopolymerized Copper-Catalyzed Azide–Alkyne (CuAAC) Networks. Macromolecules, 49(4), 1191-1200.

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Thiolated Perfluorinated Polymer Synthesis

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Chloroform (CHCl₃), methanol (MeOH) and dichloromethane (CH₂Cl₂) were obtained from Carlo Erba (Val de Reuil, France). Dialysis membranes (MWCO 1 and 6–8 KDa) were procured from Spectrumlabs. Polyethylene glycol 550 monomethyl ether and 4-toluenesulfonyl chloride (TsCl) were obtained from Fluka (Buchs, Switzerland), potassium thioacetate and 4-dimethylamino pyridine (DMAP) were purchased from Sigma Aldrich (Burlington, MA, USA). Perfluorodecan-1-thiol was purchased from ELF-Atochem (Colombes, France), perfluorooctan-1-thiol and perfluorooctyl bromide from Sigma Aldrich (Burlington, MA, USA) and trifluoropropan-1-thiol from Fluorochem (Glossop, UK).

Le Gal M., Renard E., Simon-Colin C., Larrat B, & Langlois V. (2021). Amphiphilic and Perfluorinated Poly(3-Hydroxyalkanoate) Nanocapsules for 19F Magnetic Resonance Imaging. Bioengineering, 8(9), 121.

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Characterization of Synthesized Compounds

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The UV-Visible and the Fluorescence spectra of the synthesized compounds were recorded on Shimadzu UV 1601 PC and on PerkinElmer LS45 spectrofluorimeter respectively. The TEM was done with JEOL JEM-100-CX-II and the XRD on Phillips X'Pert Pro. ¹³C and ¹H-NMR spectra were obtained using Bruker Avance III 400 MHz NMR in CDCl₃ with tetramethylsilane as internal standard. Coumarin, potassium thioacetate, KOH, silver nitrate were from Sigma Aldrich. All solvents were purchased from Merck. All chemicals were used as received.

Paul S., Chakraborty B.B., Anwar S., Paul S.B, & Choudhury S. (2020). Self-assembly of silver nanoparticles through functionalization with coumarin-thiazole fused-ring thiol. Heliyon, 6(4), e03674.

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Doxorubicin-loaded Hydrogel Bladder Delivery

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Materials 2-Hydroxyethyl methacrylate (HEMA) was a gift from Vista Optics (UK). 2-Bromoethanol, ethylene glycol dimethacrylate, potassium thioacetate, L-cysteine hydrochloride, doxorubicin hydrochloride, Tris-buffered saline, FITC-dextran (10 kDa) and 5,5 0 -dithiobis-(2-nitrobenzoic acid) were purchased from Sigma-Aldrich (UK). Sodium thiomethoxide and acryloyl chloride were purchased from Alfa Aesar (UK). Dialysis membranes (12-14 kDa MWCO) were purchased from Visking (UK). Triethylamine was dried over 3 Å molecular sieves before use. 2-Hydroxyethyl methacrylate was purified by vacuum distillation, all other reagents were used without further purification. Artificial urine was composed of sodium chloride (105.5 mM), potassium chloride (63.7 mM), sodium citrate dihydrate (3.2 mM), sodium dihydrogen phosphate (3.2 mM) and sodium sulfate (17 mM). 21 Porcine bladder tissues were received from PC Turner abattoir (Farmborough, UK), taken on the day of slaughter, and dissected to yield approximately 2 Â 2 cm 2 squares of internal mucosa, which were frozen in cling-film and stored at À20 1C.

Cook MT ., Schmidt SA ., Lee E ., Samprasit W ., Opanasopit P , & Khutoryanskiy VV . (2015). Synthesis of mucoadhesive thiol-bearing microgels from 2-(acetylthio)ethylacrylate and 2-hydroxyethylmethacrylate: novel drug delivery systems for chemotherapeutic agents to the bladder. Journal of materials chemistry. B, 3(32).

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