Crotonic acid

Crotonic acid
IUPAC name

(E)-but-2-enoic acid
Other names

trans-2-butenoic acid
beta-methylacrylic acid
3-methylacrylic acid
(E)-2-butenoic acid
Identifiers
CAS number 107-93-7 N
PubChem 637090
ChemSpider 552744 Y
DrugBank DB02074
ChEBI CHEBI:41131 Y
ChEMBL CHEMBL1213528 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H6O2
Molar mass 86.09 g/mol
Density 1.02 g/cm3
Melting point

70–73 °C
Boiling point

185–189 °C
Acidity (pKa) 4.69 [1]
Hazards
MSDS SIRI.org
Related compounds
Other anions crotonate
Related carboxylic acids propionic acid
acrylic acid
butyric acid
succinic acid
malic acid
tartaric acid
fumaric acid
pentanoic acid
Related compounds butanol
butyraldehyde
crotonaldehyde
2-butanone
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Crotonic acid, or trans-2-butenoic acid, is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. Crotonic acid is so named because it was erroneously thought to be a saponification product of croton oil. It crystallizes as needles from hot water.

Racemic threonine can be prepared from crotonic acid by alpha-functionalization using mercury(II) acetate.[2]

See also

References

  1. ^ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  2. ^ Carter, H. E.; West, H. D. (1955), "dl-Threonine", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0813 ; Coll. Vol. 3: 813 

 This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.