Copper bis(2-ethylhexanoate)

Catalog NumberHG149111

CAS Number149-11-1

CategoryAnionic Surfactants

Synonyms

Hexanoic acid, 2-ethyl-, copper (2+) salt

Molecular Weight

349.95

Molecular Formula

C16H30CuO4

Appearance

Solid

Application

Use as emulsifying agent, dispersing agent.; Use as antibacterial agent, preservative.

Active Content

95%

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Case Study

Copper(II) 2-Ethylhexanoate-Promoted Stereoselective Alkene Oxyamination for Morpholine Synthesis

Sequeira, Fatima C., et al. Organic letters 14.17 (2012): 4482.

Copper(II) 2-ethylhexanoate [Cu(eh)₂] was used as a highly soluble copper(II) promoter for a stereoselective alkene oxyamination that installs an alcohol and an amine across a double bond, generating 2-aminomethyl morpholines valuable in drug discovery.
Experimental Protocol: β-Hydroxy N-allylsulfonamide 1a (0.116 mmol) was treated with Cu(eh)₂, Cs₂CO₃ (1 equiv) and TsNH₂ (1.5 equiv) in xylenes (0.1 M) at 130 °C for 24 h; sulfonamide, benzamide and azide nucleophiles were explored. Diastereoselectivity was measured by ¹H NMR, and morpholine 2n was confirmed by X-ray crystallography.
Performance Evaluation: In this reaction the alcohol adds intramolecularly while the amine couples intermolecularly. Optimal conditions (2 equiv Cu(eh)₂, xylenes, 130 °C) gave morpholine 2a in 87% yield as a single diastereomer (>20:1 dr). Substrate scope delivered yields of 42-83% (SESNH₂ 98%, NaN₃ 53%), while a 1,1-disubstituted alkene gave the highly substituted morpholine 6 in 91% yield as a 2:1 mixture. In the absence of an amine, dioxygenation produced 2-ethylhexanoic esters, and 2-aminomethyl tetrahydrofurans formed in 83-85% yield.

Copper(II) 2-Ethylhexanoate as Optimal Catalyst for Redox-Neutral alpha-Alkynylation of Amines

Das, Deepankar, et al. Angewandte Chemie (International ed. in English) 52.13 (2013): 3765.

Copper(II) 2-ethylhexanoate [Cu(2-EH)₂] was identified as the optimal catalyst for a redox-neutral, three-component alpha-alkynylation of amines with aldehydes and alkynes, giving ring-substituted propargylic amines.
Experimental Protocol: A 10 mL microwave tube was charged with a SiC passive heating element, Cu(II) 2-ethylhexanoate (0.15 equiv), toluene (1 mL), alkyne (1.5 equiv), amine (1.5 equiv) and aldehyde (0.25 mmol), then heated at 150 °C (200 W, 30-80 psi) for 15 min and purified by silica-gel chromatography; a reflux alternative was also tested. Fourteen catalysts were surveyed against 2,6-dichlorobenzaldehyde, pyrrolidine and phenylacetylene.
Performance Evaluation: Cu(2-EH)₂ gave the best 6a/7a ratio of 20:1 at 82% yield, outperforming CuBr (1:5), Cu(OAc)₂ (7:1, 47%) and Cu(OTf)₂ (5:1, 45%); no product formed without catalyst or with 2-ethylhexanoic acid. Lowering the concentration from 0.5 to 0.25 M improved the ratio to >25:1 at 81% yield, and refluxing gave 19:1 and 86% in 30 min. Steric factors dominated regioselectivity, with mesitaldehyde reaching 11:1. Piperidine, azepane, morpholine and N-methylbenzylamine were also coupled, demonstrating broad synthetic scope.

• Synonyms: Hexanoic acid, 2-ethyl-, copper (2+) salt
• Molecular Weight: 349.95
• Molecular Formula: C16H30CuO4
• Appearance: Solid
• Application: Use as emulsifying agent, dispersing agent.; Use as antibacterial agent, preservative.
• Active Content: 95%