Tetrolic acid
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| Names | |
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Preferred IUPAC name
But-2-ynoic acid
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| Other names
2-Butynoic acid
But-2-ynoic acid Butynoic acid |
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| Identifiers | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C4H4O2 | |
| Molar mass | 84.07 g·mol−1 |
| Density | 0.9641 g/cm3 |
| Melting point | 78 °C (172 °F; 351 K) |
| Boiling point | 203 °C (397 °F; 476 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
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.
The first reported synthesis 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 on a commercial scale by treatment of propyne with a strong base (to form an acetylide), followed by carbon dioxide:
Strong bases such as n-BuLi and NaNH2 can be used.
Tetrolic acid is highly soluble in polar solvents (water, ethanol) and may be recrystallized from non polar solvents (such as heptane, toluene). The compound is a white crystalline solid which can exist in two polymorphous crystalline forms.
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.
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