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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/REAXYS Number:
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.

signalword

Warning

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

111.2 °F - closed cup

flash_point_c

44 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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
G Casperson et al.
Journal of basic microbiology, 26(5), 259-269 (1986-01-01)
Analogs of the natural substance (E)-hex-2-en-1-al which occurs naturally in green plants and is known to have microbiocidal properties were synthesized and studied with respect to their antifungal properties. Saturated and unsaturated aldehydes, alcohols, carbon acids and enolacetate were tested
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)
Continuous catalytic ?one-pot? multi-step synthesis of 2-ethylhexanal from crotonaldehyde
Seki T, et al.
Chemical Communications (Cambridge, England), 3562-3564 (2007)
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)
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