| Crotonaldehyde[1] | |
|---|---|
|
(2E)-but-2-enal |
|
|
Other names
Crotonaldehyde |
|
| Identifiers | |
| CAS number | 4170-30-3 |
| PubChem | 447466 |
| ChemSpider | 394562 |
| DrugBank | DB04381 |
| KEGG | C19377 |
| ChEBI | CHEBI:41607 |
| ChEMBL | CHEMBL1086445 |
| 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 |
3
4
2
|
| Related compounds | |
| Related alkenals | Acrolein |
| (verify) (what is: /?) 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 |
Crotonaldehyde is produced by the aldol condensation of acetaldehyde:
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]
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.