Isocrotonic acid

Isocrotonic acid (also known as quartenylic acid; formally named (Z)-2-butenoic acid) is the cis isomer of crotonic acid. It is an oil, possessing a smell similar to that of brown sugar. It boils at 171.9 °C, concomitant with conversion into crotonic acid. Isomerization is complete when the cis acid is heated to 170–180 °C in a sealed tube.

Isocrotonic acid
Names
Preferred IUPAC name
(2Z)-But-2-enoic acid
Other names
(Z)-But-2-enoic acid
(Z)-2-Butenoic acid
cis-2-Butenoic acid
cis-β-Methylacryllic acid
(Z)-β-Methylacryllic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.249
EC Number
  • 207-973-2
UNII
Properties
C4H6O2
Molar mass 86.090 g·mol−1
Density 1.03 g·cm−3 [1]
Melting point 15 °C (59 °F; 288 K)[1]
Boiling point 168 to 169 °C (334 to 336 °F; 441 to 442 K)[1]
Related compounds
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).
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Infobox references

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.[2]

(Z)-(C6H5)CH=CHCH2COOH     α-naphthol   +   H2O

References

  1. The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14. Auflage, 2006, S. 894, ISBN 978-0-911910-00-1.
  2. Fittig, Rudolph; Erdmann, Hugo (1883). "Synthese des α-Naphtols" [Synthesis of α-Naphtol]. Ber. Dtsch. Chem. Ges. (in German). 16 (1): 43–44. doi:10.1002/cber.18830160115.
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