Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
Tetrolic acid (2-butynoic acid) is a short-chain unsaturated carboxylic acid, described by the formula CH3−C≡C−CO2H. Salts and esters of tetrolic acid are known as tetrolates.
Names | |
---|---|
Preferred IUPAC name
But-2-ynoic acid | |
Other names
2-Butynoic acid Butynoic acid | |
Identifiers | |
3D model (JSmol) |
|
ChemSpider | |
ECHA InfoCard | 100.008.815 |
PubChem CID |
|
UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
CH3C≡CCO2H | |
Molar mass | 84.074 g·mol−1 |
Density | 0.9641 g/cm3[1] |
Melting point | 78 °C (172 °F; 351 K)[1] |
Boiling point | 203 °C (397 °F; 476 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
The first reported synthesis[2] of tetrolic acid is believed to be by German chemist Johann Georg Anton Geuther in 1871 as part of his work investigating the derivatives of ethyl acetoacetate.
Tetrolic acid is manufactured[3] on a commercial scale by treatment of propyne with a strong base (to form an acetylide), followed by carbon dioxide:
Tetrolic acid is highly soluble in polar solvents (water, ethanol) and can be recrystallized from non-polar solvents (such as heptane, hexane or toluene). The compound is a white crystalline solid which can exist in two polymorphous crystalline forms.[6]
The proton nuclear magnetic resonance (1H-NMR) spectrum in deuterated dimethyl sulfoxide shows a characteristic singlet peak at 1.99 ppm corresponding to the –CH3 protons.
Tetrolic acid sublimes at temperatures above 20°C, and should ideally be stored in a sealed container in a refrigerator.[7]
Accelerated rate calorimetry (ARC) showed exothermic onset from 135 °C, precluding short-path distillation as a means of purification.[7]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.