Acetylenedicarboxylic acid

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Acetylenedicarboxylic acid[1]
Structural formula of acetylenedicarboxylic acid
Ball-and-stick model
Identifiers
CAS number 142-45-0 YesY
PubChem 371
ChemSpider 362 YesY
KEGG C03248 YesY
ChEBI CHEBI:30781 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H2O4
Molar mass 114.06 g mol−1
Appearance Crystalline solid
Melting point 175–176 °C (dec.)[2]
180–187 °C (dec.)[1]
Hazards
R-phrases R25 R36/37/38
S-phrases S26 S45
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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 C4O42−, 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.[2][3][4] 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.[2]

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[edit]

References[edit]

  1. ^ a b Acetylenedicarboxylic acid at Sigma-Aldrich
  2. ^ a b c Abbott, T. W.; Arnold, R. T.; Thompson, R. B., "Acetylenedicarboxylic acid", Org. Synth. ; Coll. Vol. 2: 10 
  3. ^ Bandrowski, E. (1877). "Ueber Acetylendicarbonsäure". Berichte der deutschen chemischen Gesellschaft 10: 838. doi:10.1002/cber.187701001231. 
  4. ^ E. Bandrowski (1879). "Weitere Beiträge zur Kenntniss der Acetylendicarbonsäure". Berichte der deutschen chemischen Gesellschaft 12 (2): 2212–2216. doi:10.1002/cber.187901202261.