Crotonaldehyde
| Skeletal formula of crotonaldehyde | |
| Ball-and-stick model of (Z)-crotonaldehyde | |
| Names | |
|---|---|
| IUPAC name
(2E)-but-2-enal
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| Other names
Crotonaldehyde
Crotoinic aldehyde β-Methacrolein β-Methyl acrolein 2-butenal Propylene aldehyde |
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| Identifiers | |
4170-30-3  123-73-9 (E) 15798-64-8 (Z) |
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| ChEBI | CHEBI:41607  |
| ChEMBL | ChEMBL1086445 |
| ChemSpider | 394562 |
| DrugBank | DB04381 |
| EC Number | 204-647-1 |
| 6288 | |
| Jmol 3D model | Interactive image |
| KEGG | C19377 |
| PubChem | 447466 |
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| Properties | |
| 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) |
| 18% (20°C)[2] | |
| Solubility | very soluble in ethanol, ethyl ether, acetone soluble in chloroform miscible in benzene |
| Vapor pressure | 19 mmHg (20°C)[2] |
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Refractive index (nD)
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1.4362 |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related alkenals
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Acrolein |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| 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.[3]
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.[3]
Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is an excellent prochiral dienophile.[4] It is a Michael acceptor. Addition of methylmagnesium chloride affords 3-penten-2-ol.[5]
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. It is used to make preservatives.
See also
References
- ↑ Merck Index, 11th Edition, 2599
- ↑ 2.0 2.1 Cite error: Invalid
<ref>tag; no text was provided for refs namedPGCH - ↑ 3.0 3.1 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
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External links
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