Names | |
---|---|
Preferred IUPAC name
3-Hydroxybutanal
[1] | |
Other names
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.003.210 |
EC Number |
|
MeSH | 3-hydroxybutanal |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 their
standard state (at 25 °C [77 °F], 100 kPa).
|
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. [2] The compound is chiral although this aspect is not often exploited.
Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide: [2]
This is the prototypical aldol reaction.
Dehydration of 3-hydroxybutanal gives crotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion: [2]
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.
Aldol has been used in making perfumes and in ore flotation. [3]
It was formerly used in medicine as a hypnotic and sedative. [4]
Names | |
---|---|
Preferred IUPAC name
3-Hydroxybutanal
[1] | |
Other names
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.003.210 |
EC Number |
|
MeSH | 3-hydroxybutanal |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 their
standard state (at 25 °C [77 °F], 100 kPa).
|
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. [2] The compound is chiral although this aspect is not often exploited.
Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide: [2]
This is the prototypical aldol reaction.
Dehydration of 3-hydroxybutanal gives crotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion: [2]
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.
Aldol has been used in making perfumes and in ore flotation. [3]
It was formerly used in medicine as a hypnotic and sedative. [4]