Isocrotonic acid (also known as quartenylic acid; formally named (Z)-2-butenoic acid) is the cis isomerofcrotonic acid. It is an oil, possessing an odor similar to that of brown sugar. At its boiling point of 171.9 °C, it converts into crotonic acid. The compound can be prepared from 1,3‑dibromo-2‑butanone via the Favorskii rearrangement.[2]
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Preferred IUPAC name
(2Z)-But-2-enoic acid | |
Other names
(Z)-But-2-enoic acid | |
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ECHA InfoCard | 100.007.249 |
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Properties | |
C4H6O2 | |
Molar mass | 86.090 g·mol−1 |
Density | 1.03 g·cm−3 [1] |
Melting point | 12.5–14 °C (54.5–57.2 °F; 285.6–287.1 K)[2] |
Boiling point | 168 to 169 °C (334 to 336 °F; 441 to 442 K)[1] |
Related compounds | |
Related carboxylic acids |
Crotonic acid (trans isomer) Angelic acid Senecioic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Ethyl isocrotonate can be prepared by semihydrogenationofethyl tetrolate.[3]
Rudolph Fittig and Hugo Erdmann showed that the γ-phenyl structural analog of isocrotonic acid forms α-naphthol when dehydrated, an observation that provided useful evidence in understanding the nature of naphthalene.[4]
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