Crotonaldehyde

From Wikipedia, the free encyclopedia
Crotonaldehyde[1]
IUPAC name

(2E)-but-2-enal

Other names

Crotonaldehyde
crotoinic aldehyde
β-Methacrolein

Identifiers
CAS number 4170-30-3 N, 123-73-9 (E) YesY, 15798-64-8 (Z) YesY
PubChem 447466
ChemSpider 394562 YesY
EC number 204-647-1
DrugBank DB04381
KEGG C19377 N
ChEBI CHEBI:41607 YesY
ChEMBL CHEMBL1086445 YesY
Jmol-3D images Image 1
Properties
Molecular formula C4H6O
Molar mass 70.09 g mol−1
Appearance colourless liquid
Odor pungent, suffocating odor
Density 0.846 g/cm3
Melting point −76.5 °C; −105.7 °F; 196.7 K
Boiling point 104.0 °C; 219.2 °F; 377.1 K
Solubility very soluble in ethanol, ethyl ether, acetone
soluble in chloroform
miscible in benzene
Refractive index (nD) 1.4362
Hazards
R-phrases R11 R24/25 R26 R37/38 R41 R48/22 R50 R68
S-phrases S26 S28 S36/37/39 S45 S61
NFPA 704
3
4
2
Flash point 13 °C; 55 °F; 286 K
Autoignition temperature 207 °C; 405 °F; 480 K
Explosive limits 2.95-15.5%
Related compounds
Related alkenals Acrolein

cis-3-hexenal
(E,E)-2,4-Decadienal

 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.[2]

Production and uses

Crotonaldehyde is produced by the aldol condensation of acetaldehyde:

2 CH3CHO → CH3CH=CHCHO + H2O

Its main application is as a precursor to fine chemicals. Sorbic acid, a food preservative, and trimethylhydroquinone, a precursor to the vitamin E, are prepared from crotonaldehyde. Other derivatives include crotonic acid and 3-methoxybutanol.[2]

Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is an excellent prochiral dienophile.[3] It is a Michael acceptor. Addition of methylmagnesium chloride affords 3-penten-2-ol.[4]

Safety

Crotonaldehyde is an irritant. It is listed as an "extremely hazardous substance" as defined by the U.S. Emergency Planning and Community Right-to-Know Act. It occurs widely in nature.

See also

References

  1. ↑ Merck Index, 11th Edition, 2599
  2. ↑ 2.0 2.1 R. P. Schulz, J. Blumenstein, C. Kohlpaintner "Crotonaldehyde and Crotonic Acid" Ullmann's Encyclopedia of Chemical Technology, Wiley-VCH, Weinheim: 2005. doi:10.1002/14356007.a08_083
  3. ↑ Longley, Jr., R. I..; Emerson, W. S.; Blardinelli, A. J. (1963), "3,4-Dihydro-2-methoxy-4-methyl-2H-pyran", Org. Synth. ; Coll. Vol. 4: 311 
  4. ↑ Coburn, E. R. (1955), "3-Penten-2-ol", Org. Synth. ; Coll. Vol. 3: 696 

External links

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