|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||88.106 g·mol−1|
|Boiling point||162 °C (324 °F; 435 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
3-Hydroxybutanal (acetaldol) is an organic compound with the formula CH3CH(OH)CH2CHO. It is classified as an aldol, formally the product of the dimerization of acetaldehyde. A colorless liquid, it is a versatile and valuable intermediate with diverse impacts. The compound is chiral although this aspect is not often exploited.
Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide:
Dehydration of 3-hydroxybutanal gives crotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion:
Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:
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.
It was formerly used in medicine as a hypnotic and sedative.