Propionaldehyde

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Propionaldehyde
IUPAC name	Propionaldehyde
Systematic name	Propanal
Other names	Methylacetaldehyde; propionic aldehyde; propaldehyde
Identifiers
CAS number	[123-38-6]
UN number	1275
SMILES	CCC=O
Properties
Molecular formula	C3H6O
Molar mass	58.080 g mol−1
Appearance	Colorless liquid Pungent, marty 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

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

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

[edit] Uses

It is principally used as a precursor to "trimethylolethane" (CH₃C(CH₂OH)₃) through a condensation reaction with methanol; this triol is an important intermediate in the production of alkyd resins.

Condensation of propionaldehyde with tert-butylamine gives CH₃CH₂CH=N-t-Bu, a three-carbon building block used in organic synthesis. Deprotonation of this imine with LDA produces CH₃CHLiCH=N-t-Bu, which in turn condenses with aldehydes.^[1]

[edit] 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.