3-Hydroxybutanal

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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.

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) Y
  • 117706-97-5 (R) Y
  • 117706-98-6 (S) Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 7609 (R/S) Y
  • 18915429 (R) Y
ECHA InfoCard 100.003.210
EC Number
  • 203-530-2
MeSH 3-hydroxybutanal
PubChem CID
  • 7897 (R/S)
  • 13061653 (R)
UNII
  • 8C6G962B53 N
CompTox Dashboard (EPA)
  • DTXSID2050407
InChI
  • InChI=1S/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3 Y
    Key: HSJKGGMUJITCBW-UHFFFAOYSA-N Y
  • InChI=1/C4H8O2/c1-4(6)2-3-5/h3-4,6H,2H2,1H3
    Key: HSJKGGMUJITCBW-UHFFFAOYAI
SMILES
  • CC(O)CC=O
Properties
Chemical formula
 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

Lactaldehyde

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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

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