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E29109

Sigma-Aldrich

2-Ethylhexanal

96%

Synonym(s):

2-Ethylcapronaldehyde

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About This Item

Linear Formula:
CH3(CH2)3CH(C2H5)CHO
CAS Number:
123-05-7
Molecular Weight:
128.21
Beilstein:
1700556
EC Number:
204-596-5
MDL number:
MFCD00006987
UNSPSC Code:
12352100
PubChem Substance ID:
24894488
NACRES:
NA.22

Quality Level

100

Assay

96%

form

liquid

impurities

<4% 2-ethylhexanoic acid

refractive index

n20/D 1.415 (lit.)

bp

55 °C/13.5 mmHg (lit.)

density

0.822 g/mL at 25 °C (lit.)

SMILES string

[H]C(=O)C(CC)CCCC

InChI

1S/C8H16O/c1-3-5-6-8(4-2)7-9/h7-8H,3-6H2,1-2H3

InChI key

LGYNIFWIKSEESD-UHFFFAOYSA-N

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General description

2-Ethylhexanal is an aliphatic aldehyde used as an intermediate to produce various useful products such as perfumes, disinfectants, paints, warning agents, insecticides, and leak detectors.

Application

2-Ethylhexanal can be used as:
  • A reductant in the Mukaiyama epoxidation of cis-cyclooctene.
  • A reactant in the Horner-Wadsworth-Emmons reaction to synthesize cis-α,β-unsaturated amides.
  • A starting material to synthesize 2-ethylhexanoic acid using manganese(II) acetate as a catalyst.

Signal Word

Warning

Hazard Statements

H226,H317,H361

Hazard Classifications

Flam. Liq. 3 - Repr. 2 - Skin Sens. 1

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

111.2 °F - closed cup

Flash Point(C)

44 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Heather L Voegtle et al.
Journal of chemical ecology, 34(2), 215-219 (2008-01-24)
E-2-ethyl-2-hexen-1-ol (1), mellein (4), and 4-hydroxymellein (5) were identified as the major volatile compounds in the head and/or thorax of Camponotus quadrisectus. Neither 1 nor 5 have been previously detected in insects. Also identified were small amounts of m-cresol (2)
Continuous catalytic ?one-pot? multi-step synthesis of 2-ethylhexanal from crotonaldehyde
Seki T, et al.
Chemical Communications (Cambridge, England), 3562-3564 (2007)
D L Wood et al.
Poultry science, 63(3), 469-477 (1984-03-01)
Di-(2-ethylhexyl) phthalate (DEHP) and three structurally related side-chain analogs were fed to laying hens to determine relationships of structure to effects on lipid metabolism. Hubbard broiler breeder hens were fed either a standard laying mash control diet or the control
Factors affecting the selectivity of air oxidation of 2-ethyhexanal, an α-branched aliphatic aldehyde
Lehtinen C and Brunow G
Organic Process Research & Development, 4, 544-549 (2000)
David M Hodgson et al.
The Journal of organic chemistry, 78(4), 1508-1518 (2013-01-30)
The synthesis and alkylation of chiral, nonracemic tropane- and homotropane-derived enamines is examined as an approach to enantioenriched α-alkylated aldehydes. The two bicyclic N auxiliaries, which differ by a single methylene group, give opposite senses of asymmetric induction on alkylation
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