3-Hydroxybutanal
Appearance
Names | |
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Preferred IUPAC name
3-Hydroxybutanal[1] | |
Other names
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Identifiers | |
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3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.003.210 |
EC Number |
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MeSH | 3-hydroxybutanal |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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
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Glycolaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In
chiral
although this aspect is not often exploited.
Production
Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide:[2]
- 2 CH3CHO → CH3CH(OH)CH2CHO + H2O
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]
- CH3CH(OH)CH2CHO → CH3CH=CHCHO + H2O
Hydrogenation of 3-hydroxybutanal gives
1,3-butanediol
:
- CH3CH(OH)CH2CHO + H2 → CH3CH(OH)CH2CH2OH
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. Retrieved 13 October 2011.
- ^ ISBN 978-3527306732.
- American Heritage Dictionary, 1973.
- ^ Hans Brandenberger, Robert A. A. Maes. (1997). Analytical Toxicology: For Clinical, Forensic, and Pharmaceutical Chemists. New York: de Gruyter.