Crotonaldehyde
Skeletal formula of crotonaldehyde | |
Ball-and-stick model of (Z)-crotonaldehyde | |
Names | |
---|---|
IUPAC name
(2E)-but-2-enal
|
|
Other names
Crotonaldehyde
Crotoinic aldehyde β-Methacrolein β-Methyl acrolein 2-butenal Propylene aldehyde |
|
Identifiers | |
4170-30-3 ![]() 123-73-9 (E) ![]() 15798-64-8 (Z) ![]() |
|
ChEBI | CHEBI:41607 ![]() |
ChEMBL | ChEMBL1086445 ![]() |
ChemSpider | 394562 ![]() |
DrugBank | DB04381 ![]() |
EC Number | 204-647-1 |
6288 | |
Jmol 3D model | Interactive image |
KEGG | C19377 ![]() |
PubChem | 447466 |
|
|
|
|
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] |
Refractive index (nD)
|
1.4362 |
Vapor pressure | {{{value}}} |
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).
|
|
![]() ![]() ![]() |
|
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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.