Crotonaldehyde


Crotonaldehyde
Crotonaldehyde[1]
Identifiers
CAS number 4170-30-3 N
PubChem 447466
ChemSpider 394562 YesY
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 Colorless liquid
Density 0.846 g/cm3
Melting point

-76.5 °C, 197 K, -106 °F

Boiling point

104.0 °C, 377 K, 219 °F

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
NFPA 704.svg
3
4
2
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, 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]

Contents

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. ^ a b 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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV4P0311 ; Coll. Vol. 4: 311 
  4. ^ Coburn, E. R. (1955), "3-Penten-2-ol", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV3P0696 ; Coll. Vol. 3: 696 

External links


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Look at other dictionaries:

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  • crotonaldehyde — krotono aldehidas statusas T sritis chemija formulė CH₃CH=CHCHO atitikmenys: angl. crotonaldehyde rus. кротоновый альдегид ryšiai: sinonimas – 2 butenalis …   Chemijos terminų aiškinamasis žodynas

  • crotonaldehyde — /kroht n al deuh huyd /, n. Chem. a whitish liquid with pungent and suffocating odor, C4H6O, soluble in water, used as a solvent, in tear gas, and in organic synthesis. Also called betamethyl acrolein, crotonic aldehyde. [croton(ic) (see CROTONIC …   Universalium

  • crotonaldehyde — noun The unsaturated aliphatic aldehyde CH CH=CH CHO that is used in organic synthesis …   Wiktionary

  • crotonaldehyde — cro·ton·aldehyde …   English syllables

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