2-ethylhexanoic acid

2-Ethylhexanoic acid

Names
IUPAC name 2-Ethylhexanoic acid
Identifiers
CAS Number	149-57-5 Y 72377-05-0 S enantiomer N 56006-48-5 R enantiomer N
3D model (Jmol)	Interactive image
Beilstein Reference	1750468
ChEMBL	ChEMBL1162485 Y ChEMBL1162487 N ChEMBL1162486 N
ChemSpider	8373 Y 70431 R N 119200 S N
ECHA InfoCard	100.005.222
EC Number	205-743-6
MeSH	2-ethylhexanoic+acid
PubChem	8697 78052 R 135309 S
RTECS number	MO7700000
UNII	01MU2J7VVZ Y
InChI InChI=1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) Y Key: OBETXYAYXDNJHR-UHFFFAOYSA-N Y
SMILES CCCCC(CC)C(O)=O
Properties
Chemical formula	C8H16O2
Molar mass	144.21 g·mol−1
Appearance	Colorless liquid
Density	903 mg mL−1
Melting point	−59.00 °C; −74.20 °F; 214.15 K
Boiling point	228.1 °C; 442.5 °F; 501.2 K
log P	2.579
Vapor pressure	<1 Pa (at 25 °C)
Acidity (pKa)	4.819
Basicity (pKb)	9.178
Refractive index (nD)	1.425
Thermochemistry
Std enthalpy of formation (ΔfHo298)	−635.1 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	-4.8013–4.7979 MJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H312, H318, H361
GHS precautionary statements	P280, P305+351+338
EU classification (DSD)	Xn
R-phrases	R20/21/22, R37/38, R41, R63
S-phrases	(S2), S26, S36/37/39
Flash point	114 °C (237 °F; 387 K)
Autoignition temperature	371 °C (700 °F; 644 K)
Explosive limits	0.9–6.7%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	1.142 g kg−1(dermal, rabit) 3 g kg−1(oral, rat)
Related compounds
Related compounds	2-Methylhexane 3-Methylhexane Valnoctamide 2-Methylheptane 3-Methylheptane 2-Ethylhexanol Valpromide Propylheptyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

2-Ethylhexanoic acid is the organic compound with the formula CH₃(CH₂)₃CH(C₂H₅)CO₂H. It is a carboxylic acid that is widely used to prepare lipophilic metal derivatives that are soluble in nonpolar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.

2-Ethylhexanoic acid is produced industrially in two steps from butyraldehyde. Aldol condensation of the aldehyde gives 2-ethylhexanal. Oxidation of the latter gives the carboxylic acid.

These lipophilic metal-containing derivatives are used in many ways as catalysts in polymerizations, oxidation (drying agents), and organic synthesis. The high solubility of these metal complexes is attributable to the long hydrocarbon chain and the presence of a chiral center which leads to mixtures of enantiomeric complexes. These metal complexes, which exist as mixtures of several diastereoisomer, are often described as salts. They are, however, not ionic but charge-neutral coordination complexes. Their structures are akin to the corresponding acetates.