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Propionaldehyde



Propionaldehyde
IUPAC name Propionaldehyde
Systematic name Propanal
Other names Methylacetaldehyde; propionic aldehyde; propaldehyde
Identifiers
CAS number 123-38-6
SMILES CCC=O
Properties
Molecular formula C3H6O
Molar mass 58.080 g mol−1
Appearance Colorless liquid
Pungent, fruity odor
Density 0.81 g cm−3
Melting point

−81 °C (192 K)

Boiling point

46-50 °C (321 K)

Solubility in water 20 g/100 mL
Viscosity 0.6 cP at 20°C
Structure
Molecular shape C1, O: sp2

C2, C3: sp3

Dipole moment 2.52 D
Hazards
EU classification Highly flammable (F)
Irritant (Xi)
NFPA 704
3
2
2
 
R-phrases R11, R36/37/38
S-phrases S9, S16, S29
Flash point −26 °C
Autoignition
temperature
175 °C
Related Compounds
Related aldehydes Formaldehyde
Acetaldehyde
Butyraldehyde
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references
Note that propanol is a different compound.

Propionaldehyde is the organic compound with the formula CH3CH2CHO. It is the only 3-carbon aldehyde and is a structural isomer of acetone. It is a colourless liquid with a slightly irritating, fruity odour.

Additional recommended knowledge

Propionaldehyde is mainly produced through the hydroformylation, by combining synthesis gas (carbon monoxide and hydrogen) with ethylene using a metal catalyst:

CO + H2 + C2H4 → CH3CH2CHO

Uses

It is principally used to make trimethylolethane through a condensation reaction with methanol; this process is important in the production of alkyd resins.

Condensation of propionaldehyde with tert-butylamine gives CH3CH2CH=N-t-Bu, a useful three-carbon building block in organic synthesis. Deprotonation of this imine with LDA produces CH3CHLi2CH=N-t-Bu, which in turn condenses with aldehydes.[1]

References

  1. ^ Peralta, M. M. "Propionaldehyde t-Butylimine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Propionaldehyde". A list of authors is available in Wikipedia.
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