928-04-1

Basic information

• Product Name: Acetylenedicarboxylic acid monopotassium salt
• Synonyms: ##DISCONTINUED## Acetylenedicarboxylic acid monopotassium salt, 98+%;Acetylenedicarboxyli;Potassium 3-carboxyprop-2-ynoate;Monopotassium Acetylenedicarboxylate Potassium Hydrogen Acetylenedicarboxylate;potassiuM 3-carboxypropiolate;PotassiuM but-2-ynedioate;2-Butynedioic acid,potassiuM salt (1:1);TIMTEC-BB SBB008993
• CAS NO: 928-04-1
• Molecular Formula: C₄HO₄*K
• Molecular Weight: 152.15
• EINECS: 213-169-2
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives
• Mol File: 928-04-1.mol

Chemical Properties

• Melting Point: 133 °C
• Boiling Point: 362.4oC at 760 mmHg
• Flash Point: 187.2oC
• Appearance: white powder
• Storage Temp.: -20°C
• Water Solubility: slightly soluble (20 ºC)
• Stability: Stable. Incompatible with bases, reducing agents, oxidizing agents.
• BRN: 3571639
• CAS DataBase Reference: Acetylenedicarboxylic acid monopotassium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Acetylenedicarboxylic acid monopotassium salt(928-04-1)
• EPA Substance Registry System: Acetylenedicarboxylic acid monopotassium salt(928-04-1)

Safety Data

• Hazard Codes: T+
• Statements: 23/25-27-36/37/38
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: AP0700000
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 928-04-1(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Purification Methods

It is very soluble in H2O, but can be crystallised from a small volume of H2O in small crystals. These are washed with EtOH and dried over H2SO4 at 125o. [Bandrowski Chem Ber 10 841 1877, Lossen Justus Liebigs Ann Chem 272 133 1893, Beilstein 2 H 801, 2 I 317, 2 II 670, 2 III 1991, 2 IV 2290.]

InChI:InChI=1/C4H2O4.K/c5-3(6)1-2-4(7)8;/h(H,5,6)(H,7,8);/q;+1/p-2

Synthetic route

methanol (67-56-1) + acetylene dicarboxylic acid mono potassium salt (928-04-1) + cyclopenta-1,3-diene (542-92-7) → dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate (947-57-9)

Conditions	Yield
Stage #1: methanol; acetylene dicarboxylic acid mono potassium salt With hydrogenchloride In 1,4-dioxane for 0.166667h; Stage #2: cyclopenta-1,3-diene In 1,4-dioxane; methanol at 20℃; Diels-Alder Cycloaddition;	97%

ethanol (64-17-5) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → acetylenedicarboxylic acid diethyl ester (762-21-0)

Conditions	Yield
With sulfuric acid In benzene for 24h; Heating;	95%

acetylene dicarboxylic acid mono potassium salt (928-04-1) → α-Iodofumaric acid (5029-68-5)

Conditions	Yield
	85%
With hydrogen iodide

acetylene dicarboxylic acid mono potassium salt (928-04-1) → trans-2,3-dibromobutenedioic acid (608-38-8)

Conditions	Yield
With bromine; sodium bromide; potassium hydroxide In water at 20℃; for 24h;	80.47%
Stage #1: acetylene dicarboxylic acid mono potassium salt With bromine; potassium hydroxide Stage #2: With hydrogenchloride

acetylene dicarboxylic acid mono potassium salt (928-04-1) + cyclopenta-1,3-diene (542-92-7) → bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid (15872-28-3)

Conditions	Yield
With hydrogenchloride In water at 25℃; for 4h; Diels-Alder Cycloaddition;	79%
With hydrogenchloride In water for 0.333333h; Ambient temperature;	38%

acetylene dicarboxylic acid mono potassium salt (928-04-1) → Propiolsaeure (3634-35-3)

Conditions	Yield
With water-d2 at 100℃; for 2h;	78%

chloro-trimethyl-silane (75-77-4) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → Acetylenedicarboxylic acid monotrimethylsilyl ester (78619-83-7)

Conditions	Yield
In benzene 1.) cooled (freezing mixture), 10 min, 2.) reflux, 5 h;	60%

acetylene dicarboxylic acid mono potassium salt (928-04-1) → <3-2H>propiolic acid (18910-53-7)

Conditions	Yield
With water-d2 a) from RT to reflux, 2 h, b) reflux, 1 h;	54%
With water-d2 for 2h; Heating;

methanol (67-56-1) + ammonium hexafluorophosphate + RuCl(PPh3)2Cp + acetylene dicarboxylic acid mono potassium salt (928-04-1) → (η-cyclopentadienyl)(methoxy(methyl)carbene)bis(triphenylphosphine)ruthenium(II) hexafluorophosphate

Conditions	Yield
In neat (no solvent) for 6h; Inert atmosphere; Reflux;	53%

(hydrotris(3,5-dimethyl-1-pyrazolyl)borate)V(O)(Cl)(3,5-dimethylpyrazole) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → {VO((N2(CCH3)2CH)3BH)(HN2(CCH3)2CH)}2(OOCC2COO)*2CH3CN*2H2O

Conditions	Yield
In water; acetonitrile addn. of potassium salt in water to V-complex in MeCN, stirring (room temp., 3h), pptn.; filtration off, washing (water, MeCN, Et2O), drying (desiccator, 2 h), recrystn. (CH2Cl2/toluene 1/1 v/v); elem. anal.;	51%

acetylene dicarboxylic acid mono potassium salt (928-04-1) → 2,2,3,3-tetradeuterio-succinic acid (14493-42-6)

Conditions	Yield
With potassium hydroxide; sodium amalgam; water-d2 1.) water, room temperature, 2 d, 2.) 1 h; Multistep reaction;

acetylene dicarboxylic acid mono potassium salt (928-04-1) → C4O4(2-)*Ba(2+) (82203-73-4)

Conditions	Yield
With sodium hydroxide; barium(II) chloride Multistep reaction;

acetylene dicarboxylic acid mono potassium salt (928-04-1) + water (7732-18-5) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + propargylacidic potassium

acetylene dicarboxylic acid mono potassium salt (928-04-1) → carbon dioxide (124-38-9) + propiolate (44196-71-6)

Conditions	Yield
In water at 80℃; under 206266 Torr; Kinetics; Activation energy; Further Variations:; Temperatures;

3-hydroxy-4-propylbenzenethiol + acetylene dicarboxylic acid mono potassium salt (928-04-1) → methyl 7-hydroxy-4-oxo-6-propyl-4H-1-benzothiopyran-2-carboxylate

Conditions	Yield
With hydrogenchloride; chlorosulfonic acid; potassium hydroxide In methanol; dichloromethane; water; Petroleum ether

acetylene dicarboxylic acid mono potassium salt (928-04-1) + Thiosalicylic acid (147-93-3) → 2-carboxyphenylthiofumaric acid

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate In water

4-ethoxy-benzenethiol (699-09-2) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → 4-Ethoxyphenylthiofumaric acid

Conditions	Yield
In water

4-sulfanylphenol (637-89-8) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → 4-hydroxyphenylthiofumaric acid

Conditions	Yield
With potassium hydroxide In water

acetylene dicarboxylic acid mono potassium salt (928-04-1) + para-nitrobenzenethiol (1849-36-1) → 4-nitrophenylthiofumaric acid

Conditions	Yield
With potassium hydroxide In water

acetylene dicarboxylic acid mono potassium salt (928-04-1) + 2,4-diisopropylthiophenol (42369-42-6) → 2,4-di-isopropylphenylthiofumaric acid

Conditions	Yield
With potassium hydroxide In water

2,5-dimethoxythiophenol (1483-27-8) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → 2,5-dimethoxyphenylthio fumaric acid

Conditions	Yield
With potassium hydroxide In water

2,5-Diethoxythiophenol (29236-93-9) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → 2,5-diethoxyphenylthio fumaric acid

Conditions	Yield
With potassium hydroxide In water

5-(3-methylbutoxy)-2-propylthiophenol (42369-53-9) + acetylene dicarboxylic acid mono potassium salt (928-04-1) → [5-(3-methylbutoxy)-2-propylphenylthio] fumaric acid

Conditions	Yield
With potassium hydroxide In water

Upstream product

• 526-78-3 2,3-dibromosuccinic acid 
• 127-08-2 potassium acetate 
• 142-45-0 Acetylenedicarboxylic acid 

Downstream Products

• 4598-47-4 dioxanyl radical 
• 117831-79-5 C₈H₉O₆ 
• 117831-78-4 C₈H₉O₆ 
• 117831-80-8 C₁₂H₁₁O₁₀ 
• 53318-26-6 meso-2,3-bis(acetylthio)succinic acid 
• 17660-55-8 dl-2,3-bis(acetylthio)succinic acid 
• 7558-02-3 potassium bromide 
• 471-25-0 Propiolic acid 
• 15872-28-3 bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 

Relevant articles and documents

Environment-friendly preparation method of propiolic acid derivatives

The invention discloses an environment-friendly preparation method of propiolic acid derivatives. The preparation method comprises the following steps: (1) with 2,3-dibromosuccinic acid as a raw material, generating a butynedioic acid salt under alkaline conditions; (2) under an acidic condition, carrying out high-temperature decarboxylation to obtain propiolic acid; and (3) adding corresponding methanol or ethanol into propiolic acid in an extraction solvent, and preparing high-yield propiolate under acidic catalytic conditions under the condition that trimethyl orthoformate or triethyl orthoformate participates in dehydration. In the invention, the propiolic acid preparation method is friendly to environment and high in safety coefficient; and the method provided by the invention can beused for preparing methyl propiolate and ethyl propiolate, and has the advantages of small alcohol consumption, thorough reaction, high yield and easiness in separation.

Eu(O2C-C≡C-CO2): An EuII Containing Anhydrous Coordination Polymer with High Stability and Negative Thermal Expansion

Anhydrous EuII–acetylenedicarboxylate (EuADC; ADC2? = ?O2C-C≡C-CO2 ?) was synthesized by reaction of EuBr2 with K2ADC or H2ADC in degassed water under oxygen-free conditions. EuADC crystallizes in the SrADC type structure (I41/amd, Z=4) forming a 3D coordination polymer with a diamond-like arrangement of Eu2+ nodes (msw topology including the connecting ADC2? linkers). Deep orange coloured EuADC is stable in air and starts decomposing upon heating in an argon atmosphere only at 440 °C. Measurements of the magnetic susceptibilities (μeff=7.76 μB) and 151Eu M?ssbauer spectra (δ=?13.25 mm s?1 at 78 K) confirm the existence of Eu2+ cations. Diffuse reflectance spectra indicate a direct optical band gap of Eg=2.64 eV (470 nm), which is in accordance with the orange colour of the material. Surprisingly, EuADC does not show any photoluminescence under irradiation with UV light of different wavelengths. Similar to SrADC, EuADC exhibits a negative thermal volume expansion below room temperature with a volume expansion coefficient αV=?9.4(12)×10?6 K?1.