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| Names | |
|---|---|
| Preferred IUPAC name 3-Hydroxybutanal[1] | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.003.210 |
| EC Number |
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| MeSH | 3-hydroxybutanal |
| UNII | |
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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 | Glycolaldehyde |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Inorganic chemistry,3-hydroxybutanal (acetaldol,aldol) is anorganic compound with the formulaCH3CH(OH)CH2CHO and the structureH3C−CH(OH)−CH2−CH=O. It is classified as analdol (R−CH(OH)−CHR'−C(=O)−R") and the word "aldol" can refer specifically to 3-hydroxybutanal. It is formally the product of thedimerization ofacetaldehyde (CH3CHO). A thick colorless or pale-yellow liquid, it is a versatile and valuableintermediate with diverse impacts.[2] The compound ischiral although this aspect is not often exploited.
Acetaldehydedimerizes upon treatment with aqueoussodium hydroxide:[2]
This is the prototypicalaldol reaction.
Dehydration of 3-hydroxybutanal givescrotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion:[2]
Hydrogenation of 3-hydroxybutanal gives1,3-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.
Aldol has been used in makingperfumes and in oreflotation.[3]
It was formerly used in medicine as ahypnotic andsedative.[4]
| Authority control databases: National |
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