10387-40-3

Basic information

• Product Name: Potassium thioacetate
• Synonyms: Potasium thioacetate;Potassium thioacetat;PotassiuM thioacetate, 98% 25GR;PotassiuM thioacetate, 98% 5GR;MeCOSK;potassium 2-thioxoacetate;MERCAPTOACETIC ACID, POTASSIUM SALT;KTAA
• CAS NO: 10387-40-3
• Molecular Formula: C₂H₃KOS
• Molecular Weight: 114.21
• EINECS: 233-848-7
• Product Categories: Pharmaceutical intermediates
• Mol File: 10387-40-3.mol

Chemical Properties

• Melting Point: 173-176 °C(lit.)
• Boiling Point: 130.6 °C at 760 mmHg
• Flash Point: 32.8 °C
• Appearance: White to light brown/Crystalline Powder, Crystals or Chunks
• Density: 1.046 g/cm³
• Storage Temp.: Refrigerator (+4°C)
• Solubility: soluble
• Water Solubility: soluble
• Sensitive: Air Sensitive & Hygroscopic
• BRN: 3595448
• CAS DataBase Reference: Potassium thioacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium thioacetate(10387-40-3)
• EPA Substance Registry System: Potassium thioacetate(10387-40-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 3335
• WGK Germany: 3
• F: 3-9-13-23
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 10387-40-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Potassium thioacetate is used as a reagent for preparing thioacetate esters and other derivatives. It acts as a sulfur source in the synthesis of sulfur-containing organic compounds, which are essential for the creation of heterocycles, polymers, transition-metal ligands, nanoparticles, bioactive compounds, and macromolecular inclusion complexes.
Used in Palladium Mediated Coupling:
In the field of organic chemistry, potassium thioacetate is utilized for palladium-mediated coupling with aryl halides and triflates, leading to the formation of S-arylthioacetates and their derivatives. This process is crucial for the development of various organic compounds and materials.
Used in Conversion of Halides to Thiols:
Potassium thioacetate also serves as a reagent in the conversion of halides to thiols, which is an important transformation in organic synthesis for the production of various chemical compounds and materials.

Reactions

Thioacetate is also a class of sulfur-containing nucleophiles, of which potassium thioacetate is the most widely used reagent. Potassium thioacetate reacts with organic halides to form thioesters, which are often used as thiol-protecting groups.In the classical reaction, potassium thioacetate replaces the bromine atom to form a thiol in which the thioester formed in the first step is subjected to a nucleophilic addition elimination reaction to obtain a thiol via hydrolysis, alcoholysis or ammonolysis. Unlike the thiol formation from bromine and thiourea, this method is not strictly limited to polystyrenes. It can also be extended to poly(meth)acrylate systems. It is important that there is no observation of ester hydrolysis during the process.

InChI:InChI=1/C2H4OS.K/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1/rC2H3KOS/c1-2(4)5-3/h1H3

Synthetic route

thioacetic acid (507-09-5) → potassium thioacetate (10387-40-3)

Conditions	Yield
With potassium hydride In diethyl ether for 65h; Ambient temperature;	79%
With potassium hydroxide In ethanol at 20℃;

Ketene (463-51-4) → potassium thioacetate (10387-40-3)

Conditions	Yield
Stage #1: Ketene With hydrogen sulfide; triethylamine In butan-1-ol at -10 - -5℃; Stage #2: With potassium hydroxide In water; butan-1-ol for 1h; Heating / reflux;	63%

thioacetic acid (507-09-5) → potassium thioacetate (10387-40-3)

Conditions	Yield
With potassium hydroxide In ethanol Inert atmosphere; Schlenk technique;

1-bromo-butane (109-65-9) + potassium thioacetate (10387-40-3) → S-butyl ethanethioate (928-47-2)

Conditions	Yield
In tetrahydrofuran Reflux;	100%
With ethanol

1-Iodooctane (629-27-6) + potassium thioacetate (10387-40-3) → S-octyl thioacetate (2432-34-0)

Conditions	Yield
With silica gel In benzene at 80℃; for 3h;	100%
With silica gel In benzene at 80℃; for 3h;	100%
In various solvent(s) for 6h; Ambient temperature; Yield given;

(Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane (106502-63-0) + potassium thioacetate (10387-40-3) → Thioacetic acid S-[(1R,2S,3S,4S)-4-acetylsulfanyl-3-methoxymethoxy-2-((Z)-7-methoxymethoxy-hept-2-enyl)-cyclopentyl] ester (106502-64-1)

Conditions	Yield
In N,N-dimethyl-formamide at 64℃; for 2.5h;	100%

(S)-1-bromo-2-((S)-tert-butoxycarbonylphenylalanylamino)propane + potassium thioacetate (10387-40-3) → (S)-2-((S)-N-tert-butoxycarbonylphenylalanylamino)propyl ethanethioate

Conditions	Yield
In N,N-dimethyl-formamide for 20h; Ambient temperature;	100%

2’,3’-O-isopropylidene-5-methyl-5’-O-tosyluridine (37085-43-1) + potassium thioacetate (10387-40-3) → 5'-thioacetyl-2',3'-O-isopropylidenethymidine (161986-84-1)

Conditions	Yield
In acetone for 3h; Heating;	100%

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose (158946-12-4) + potassium thioacetate (10387-40-3) → 6-S-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-sulfo-6-thio-α-D-glucofuranose potassium salt

Conditions	Yield
In acetone Ambient temperature;	100%
In acetone Ambient temperature;

5,5-Bis(bromomethyl)[1,3]dioxane (22633-46-1) + potassium thioacetate (10387-40-3) → 5,5-Bis(acetylthiomethyl)[1,3]dioxane (361559-73-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 30h;	100%
In N,N-dimethyl-formamide at 20℃; for 24h;	82%
In N,N-dimethyl-formamide

N-(3,5-bis-{3,5-bis-[3-(adamantan-1-yloxy)-propoxy]-benzyloxy}-benzyl)-2-chloro-acetamide + potassium thioacetate (10387-40-3) → Thioacetic acid S-[(3,5-bis-{3,5-bis-[3-(adamantan-1-yloxy)-propoxy]-benzyloxy}-benzylcarbamoyl)-methyl] ester

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	100%

toluene-4-sulfonic acid 4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butyl ester (1026410-38-7) + potassium thioacetate (10387-40-3) → thioacetic acid S-[4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butyl] ester (359699-94-8)

Conditions	Yield
In acetone at 20℃; for 4h;	100%

(4R,5R)-di-tert-butyl 2,2-dioxo-1,3,2-dioxathiolane-4,5-dicarboxylate 2,2-dioxide (464189-09-1) + potassium thioacetate (10387-40-3) → (S,S)-di-tert-butyl 2-acetylsulfanyl-3-hydroxysuccinate (464189-10-4)

Conditions	Yield
Stage #1: (4R,5R)-di-tert-butyl 2,2-dioxo-1,3,2-dioxathiolane-4,5-dicarboxylate 2,2-dioxide; potassium thioacetate In acetone at 20℃; for 0.5h; Stage #2: With sulfuric acid In acetone at 20℃; for 3h; Further stages.;	100%

4-(4-bromobutoxy)biphenyl (53669-78-6) + potassium thioacetate (10387-40-3) → thioacetic acid S-[4-(biphenyl-4-yloxy)-butyl] ester (525589-30-4)

Conditions	Yield
In N,N-dimethyl-formamide	100%

11-bromo-undecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (492440-49-0) + potassium thioacetate (10387-40-3) → 11-acetylsulfanyl-undecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (492440-53-6)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In butanone at 60℃; for 3h;	100%

Upstream product

• 507-09-5 thioacetic acid 
• 507-09-5 tiolacetic acid 
• 463-51-4 Ketene 

Downstream Products

• 37180-67-9 trans-1,4-bis-(acetylsulfanyl-methyl)-cyclohexane 
• 26944-98-9 1-acetyl-6-fluoro-3-phenyl-1H-benzo[1,3,4]thiadiazine 
• 78868-96-9 7-methyl-4-acetyl-2-phenyl-4H-pyridazino<4,5-e><1,3,4>thiadiazin-8(7H)-one 
• 90330-75-9 7-phenyl-4-acetyl-2-phenyl-4H-pyridazino<4,5-e><1,3,4>thiadiazin-8(7H)-one 
• 90330-74-8 7-benzyl-4-acetyl-2-phenyl-4H-pyridazino<4,5-e><1,3,4>thiadiazin-8(7H)-one 
• 59463-56-8 thioacetic acid S-cyanomethyl ester 
• 2432-34-0 S-octyl thioacetate 
• 129301-84-4 diphenyl(thioacetoxy-S-methyl)silan 
• 63658-43-5 Methyl-6,8-diacetyldihydrolipoamid 
• 2242-70-8 Bis-acetylmercaptomethyl-sulfid 
• 38634-59-2 3,5-dithiahexan-2-one 
• 42177-11-7 (Phenylmercapto-methyl)-acetylsulfid 
• 26905-24-8 1-benzylsulfanyl-4-methoxy-benzene 
• 831-91-4 Benzyl phenyl sulfide 

Relevant articles and documents

Sulphur-sulphur, sulphur-selenium, selenium-selenium and selenium-carbon bond activation using Fe3(CO)12: An unexpected formation of an Fe2(CO)6 complex containing a μ2,κ3-C,O,Se-ligand

Three diiron hexacarbonyl complexes containing dithiolato (5), diselenolato (6), and selenolato-thiolato ligands (7), respectively, have been prepared as [FeFe]-hydrogenase mimics. Treatment of Fe3(CO)12 with one equivalent of the corresponding 5-membered heterocycles 1, 3 and 4 in toluene at reflux afforded the corresponding complexes 5-7. The reaction of 5,5-bis(bromomethyl)-2,2-dimethyl-1,3-dioxane with in situ generated Na2Se2 results in the formation of 8,8-dimethyl-7,9-dioxa-2,3-diselenaspiro[4.5]decane (1) and traces of 7,7-dimethyl-6,8-dioxa-2-selenaspiro[3.4]nonane (2). Alternatively, 5,5-bis(bromomethyl)-2,2-dimethyl-1,3-dioxane reacts with in situ generated Na2Se yielding compound 2 in 26% yield. When Fe3(CO)12 reacts under reflux with the selenaspiro compound 2 in toluene, the unique diiron complex, [Fe2(CO)6{μ2,κ3-Se,C,O-SeCH2C7H12O2}] (8), is obtained as a result of an initial selenium-carbon bond activation. Compounds 5, 6, 7, and 8 were characterized by IR, 1H, 13C{1H}, and 77Se{1H} NMR spectroscopy, mass spectrometry, elemental analysis, and X-ray single-crystal structure analysis. The chiral complex 8 shows a coordination of the O atom at the dioxane ring to one Fe atom and the O-CH- carbanionic group to the other Fe atom. Furthermore, we investigated the redox properties and the catalytic behaviour of complexes 5-8 in the presence of AcOH as a source of protons. The reduction of complexes 5-7 is accompanied by a chemical process resulting in an overall two-electron transfer at their primary reduction wave. This observation is consistent with an ECE reduction (E = electrochemical process, C = chemical process), while each reduction event in the case of complex 8 involves simple transfer of one electron. Moreover, high level DFT calculations were performed on neutral 8 and its reduction products 8- and 82-.

TETRACYCLIC TERPENE SERIES COMPOUNDS, METHODS FOR PREPARING SAME, USES THEREOF AS MEDICINES AND PHARMACEUTICAL COMPOUNDS CONTAINING SAME

The invention concerns a triterpene alkaloid of general formula (I). The invention also concerns a method for making same and use thereof as medicine.

Thioacids and thioacid salts for determining the enantiomeric excess of chiral compounds containing an electrophilic carbon center

The invention provides novel chiral compounds including 2-methoxy-2-trifluoromethylphenylacetic thioacid useful to react with and analyze other chiral compounds that have an electrophilic chiral carbon center.

METHOD FOR THE PRODUCTION OF A THIOACETIC ACID AND SALTS THEREOF

The invention relates to a method for the production of an thioacetic acid and salts thereof of formulae (I) and (II), wherein Mn+ represents ammonium or an alkali metal cation, alkaline earth metal cation, aluminium cation or titanium cation, by reacting ketene with hydrogen sulphide in the presence of a nitrogenous base or reacting ketene with an aqueous alkali metal hydrogen sulphide solution. The thioacetic acid thus formed can be, optionally, subsequently transformed into the corresponding salt by reacting it with ammonia or an alkali metal base, alkaline earth metal base, aluminium base or titanium base. The transformation of thioacetic acid and the formation of salt is carried out as a one-pot method.

A Convenient Preparation of Anhydrous Alkali Metal Thiocarboxylates

A series of alkali metal thiocarboxylates (1-5) were found to be readily obtained in high yields by the reaction of thiocarboxylic acids with metal hydrides (LiH, NaH, KH), and rubidium or caesium acetates, respectively.Their physical properties were disclosed. - Keywords: Lithium Thiocarboxylates, Sodium Thiocarboxylates, Potassium Thiocarboxylates, Rubidium Thiocarboxylates, Caesium Thiocarboxylates