Chemistry:3-Hydroxybutanal
| |
| Names | |
|---|---|
| Preferred IUPAC name
3-Hydroxybutanal[1] | |
Other names
| |
| Identifiers | |
| |
3D model (JSmol)
|
|
| ChemSpider | |
| EC Number |
|
| MeSH | 3-hydroxybutanal |
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| C4H8O2 | |
| Molar mass | 88.106 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.98 g/mL |
| Boiling point | 162 °C (324 °F; 435 K) |
| Related compounds | |
Related aldehydes
|
Glycolaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
| |
| Infobox references | |
In organic chemistry, 3-hydroxybutanal (acetaldol, aldol) is an organic compound with the formula CH
3CH(OH)CH
2CHO and the structure H
3C–CH(OH)–CH
2–CH=O. It is classified as an aldol (R–CH(OH)–CHR'–C(=O)–R") and the word "aldol" can refer specifically to 3-hydroxybutanal. It is formally the product of the dimerization of acetaldehyde (CH
3CHO). A thick colorless or pale-yellow liquid, it is a versatile and valuable intermediate with diverse impacts.[2] The compound is chiral although this aspect is not often exploited.
Production
Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide:[2]
- 2 CH
3CHO → CH
3CH(OH)CH
2CHO + H
2O
This is the prototypical aldol reaction.
Reactions and uses
Dehydration of 3-hydroxybutanal gives crotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion:[2]
- CH
3CH(OH)CH
2CHO → CH
3CH=CHCHO + H
2O
Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:
- CH
3CH(OH)CH
2CHO + H
2 → CH
3CH(OH)CH
2CH
2OH
This diol is a precursor to 1,3-butadiene, precursor to diverse polymers.
Polymerization of 3-hydroxybutanal is also spontaneous, but can be stopped with the addition of water.
Aldol has been used in making perfumes and in ore flotation.[3]
Former or niche uses
It was formerly used in medicine as a hypnotic and sedative.[4]
See also
- 4-Hydroxybutanal
References
- ↑ "3-hydroxybutanal – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7897.
- ↑ 2.0 2.1 2.2 Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen (2008). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2.
- ↑ American Heritage Dictionary, 1973.
- ↑ Hans Brandenberger, Robert A. A. Maes. (1997). Analytical Toxicology: For Clinical, Forensic, and Pharmaceutical Chemists. New York: de Gruyter.
 |  |
