Crotonaldehyde
 |
|
-Crotonaldehyde_3D_ball.png) |
|
| Names | |
|---|---|
|
IUPAC name
(2E)-but-2-enal
|
|
| Other names
Crotonaldehyde
Crotoinic aldehyde β-Methacrolein β-Methyl acrolein 2-butenal Propylene aldehyde |
|
| Identifiers | |
|
|
|
3D model (Jmol)
|
|
| ChEBI | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.021.846 |
| EC Number | 204-647-1 |
| KEGG | |
|
PubChem CID
|
|
| UNII |
|
|
|
|
|
| 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) | |
| Solubility | very soluble in ethanol, ethyl ether, acetone soluble in chloroform miscible in benzene |
| Vapor pressure | 19 mmHg (20°C) |
|
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 | |
| Flash point | 13 °C (55 °F; 286 K) |
| 207 °C (405 °F; 480 K) | |
| Explosive limits | 2.1-15.5% |
| Lethal dose or concentration (LD, LC): | |
|
LC50 (median concentration)
|
600 ppm (rat, 30 min) 1375 ppm (rat, 30 min) 519 ppm (mouse, 2 hr) 1500 ppm (rat, 30 min) |
|
LCLo (lowest published)
|
400 ppm (rat, 1 hr) |
| US health exposure limits (NIOSH): | |
|
PEL (Permissible)
|
TWA 2 ppm (6 mg/m3) |
|
REL (Recommended)
|
TWA 2 ppm (6 mg/m3) |
|
IDLH (Immediate danger)
|
50 ppm |
| Related compounds | |
|
Related alkenals
|
Acrolein |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
 (what is   ?) |
|
| Infobox references | |
cis-3-hexenal
(E,E)-2,4-Decadienal
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.
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.
Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is an excellent prochiral dienophile. It is a Michael acceptor. Addition of methylmagnesium chloride affords 3-penten-2-ol.
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.
...
Wikipedia