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Isocrotonic acid

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Isocrotonic acid
Skeletal formula
Ball-and-stick model
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-Methylacrylic acid
(Z)-β-Methylacrylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.249 Edit this at Wikidata
EC Number
  • 207-973-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2-Key: LDHQCZJRKDOVOX-IHWYPQMZSA-N
  • InChI=1/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2-Key: LDHQCZJRKDOVOX-IHWYPQMZBE
SMILES
  • C/C=C\C(=O)O
Properties
Chemical formula C4H6O2
Molar mass 86.090 g·mol
Density 1.03 g·cm
Melting point 12.5–14 °C (54.5–57.2 °F; 285.6–287.1 K)
Boiling point 168 to 169 °C (334 to 336 °F; 441 to 442 K)
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 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.

Related compounds

Ethyl isocrotonate can be prepared by semihydrogenation of ethyl tetrolate.

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.

(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. ^ C. Rappe (1973). "cis-a,b-Unsaturated Acids: Isocrotonic Acid". Organic Syntheses. 53: 123. doi:10.15227/orgsyn.053.0123.
  3. Michael J. Taschner, Terry Rosen, Clayton H. Heathcock (1986). "Ethyl Isocrotonate". Organic Syntheses. 64: 108. doi:10.15227/orgsyn.064.0108.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. 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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