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Acetylenedicarboxylic acid

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Acetylenedicarboxylic acid
Structural formula of acetylenedicarboxylic acid
Ball-and-stick model
Names
IUPAC name But-2-ynedioic acid
Other names 2-Butynedioic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.033 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)Key: YTIVTFGABIZHHX-UHFFFAOYSA-N
  • InChI=1/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)Key: YTIVTFGABIZHHX-UHFFFAOYAA
SMILES
  • C(#CC(=O)O)C(=O)O
  • O=C(O)C#CC(=O)O
Properties
Chemical formula C4H2O4
Molar mass 114.056 g·mol
Appearance Crystalline solid
Melting point 175–176 °C (dec.)
180–187 °C (dec.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Acetylenedicarboxylic acid or butynedioic acid is an organic compound (a dicarboxylic acid) with the formula C4H2O4 or HO2C-C≡C-CO2H. It is a crystalline solid that is soluble in diethyl ether.

The removal of two protons yields the acetylenedicarboxylate dianion C4O4, which consists only of carbon and oxygen, making it an oxocarbon anion. Partial ionization yields the monovalent hydrogenacetylenedicarboxylate anion HC4O4.

The acid was first described in 1877 by Polish chemist Ernest Bandrowski. It can be obtained by treating α,β-dibromosuccinic acid with potassium hydroxide KOH in methanol or ethanol. The reaction yields potassium bromide and potassium acetylenedicarboxylate. The salts are separated and the latter is treated with sulfuric acid.

Acetylenedicarboxylic acid is used in the synthesis of dimethyl acetylenedicarboxylate, an important laboratory reagent. Both the acid and the monobasic salt potassium hydrogenacetylenedicarboxylate KC4HO4 are commonly traded as laboratory chemicals.

See also

References

  1. ^ Acetylenedicarboxylic acid at Sigma-Aldrich
  2. ^ Abbott, T. W.; Arnold, R. T.; Thompson, R. B. "Acetylenedicarboxylic acid". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 2, p. 10.
  3. E. Bandrowski (1877) Ueber Acetylendicarbonsäure Chemische Berichte band 10, 838–842 (1877).
  4. E. Bandrowski (1879) Weitere Beiträge zur Kenntniss der Acetylendicarbonsäure. Berichte der deutschen chemischen Gesellschaft, volume 12, issue 2, 2212–2216. doi:10.1002/cber.187901202261
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