2-Ethylhexanal

2-Ethylhexanal

File:2-ethylhexanal.svg
Names
Preferred IUPAC name 2-Ethylhexanal
Identifiers
CAS Number	123-05-7 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87809
ChEMBL	ChEMBL1558074
ChemSpider	28981
ECHA InfoCard
EC Number	204-596-5
E number
PubChem CID	31241
UNII	SEN8S34O6U
UN number	1191
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C8H16O/c1-3-5-6-8(4-2)7-9/h7-8H,3-6H2,1-2H3 Key: LGYNIFWIKSEESD-UHFFFAOYSA-N
SMILES CCCCC(CC)C=O
Properties
Chemical formula	C8H16O
Molar mass	128.215 g·mol−1
Appearance	colorless liquid
Density	0.820 g/cm3
Melting point	< −60 °C
Boiling point	163 °C (325 °F; 436 K)
Refractive index (nD)	1.416
Hazards
GHS labelling:
Pictograms	GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word	Warning
Hazard statements	H226, H315, H317, H319, H361
Precautionary statements	P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P272, P280, P302+P352, P303+P361+P353, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)	2 2 1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Ethylhexanal is the organic compound with the formula CH₃CH₂CH₂CH₂CH(C₂H₅)CHO. A colorless liquid, it is produced on a large scale industrially as a precursor to 2-ethylhexanoic acid and 2-ethylhexanol, both used as precursors to plasticizers. It was studied in the detergent industry since the 1930s.

2-Ethylhexanal is synthesized by aldol condensation of two equivalents of butyraldehyde followed by hydrogenation of the intermediate 2-ethylhexenal. The compound is chiral, but is mainly used as a racemic mixture.

Synthesis of 2-Ethylhexanol

Synthesis of 2-Ethylhexanol

The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility. Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol. Alcohols prepared in this way are sometimes referred to as oxo alcohols. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.