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3-Hydroxybutanal

Names
Preferred IUPAC name 3-Hydroxybutanal
Other names Acetaldol 3-Hydroxybutyraldehyde beta-Hydroxybutyraldehyde β-Hydroxybutyraldehyde
Identifiers
CAS Number	107-89-1 (R/S) 117706-97-5 (R) 117706-98-6 (S)
3D model (JSmol)	Interactive image
ChemSpider	7609 (R/S) 18915429 (R)
ECHA InfoCard	100.003.210
EC Number	203-530-2
MeSH	3-hydroxybutanal
PubChem CID	7897 (R/S) 13061653 (R)
UNII	8C6G962B53
CompTox Dashboard (EPA)	DTXSID2050407
InChI InChI=1S/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3Key: HSJKGGMUJITCBW-UHFFFAOYSA-N InChI=1/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3Key: HSJKGGMUJITCBW-UHFFFAOYAI
SMILES CC(O)CC=O
Properties
Chemical formula	C4H8O2
Molar mass	88.106 g·mol
Appearance	colorless liquid
Density	0.98 g/mL
Boiling point	162 °C (324 °F; 435 K)
Related compounds
Related aldehydes	Glycolaldehyde Lactaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

In organic chemistry, 3-hydroxybutanal (acetaldol, aldol) is an organic compound with the formula CH₃CH(OH)CH₂CHO and the structure H₃C−CH(OH)−CH₂−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 (CH₃CHO). A thick colorless or pale-yellow liquid, it is a versatile and valuable intermediate with diverse impacts. The compound is chiral although this aspect is not often exploited.

Production

Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide:

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:

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.

Former or niche uses

It was formerly used in medicine as a hypnotic and sedative.

See also

• 4-Hydroxybutanal

References

1. "3-hydroxybutanal – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 13 October 2011.
2. ^ Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3527306732.
3. American Heritage Dictionary, 1973.
4. Hans Brandenberger, Robert A. A. Maes. (1997). Analytical Toxicology: For Clinical, Forensic, and Pharmaceutical Chemists. New York: de Gruyter.

• Hydroxy aldehydes
• GABA analogues
• Hypnotics
• Sedatives
• Aldols