4-({[(4-oxopent-2-en-2-yl)oxy]cuprio}oxy)pent-3-en-2-one

• ChemBase ID: 150441
• Molecular Formular: C10H14CuO4
• Molecular Mass: 261.76176
• Monoisotopic Mass: 261.01880643
• SMILES: C/C(=C\C(=O)C)/O[Cu]O/C(=C/C(=O)C)/C
• Canonical SMILES: C/C(=C\C(=O)C)/O[Cu]O/C(=C/C(=O)C)/C
• InChI: InChI=1S/2C5H8O2.Cu/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2
• InChIKey: QYJPSWYYEKYVEJ-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({[(4-oxopent-2-en-2-yl)oxy]cuprio}oxy)pent-3-en-2-one; (3E)-4-[({[(2E)-4-oxopent-2-en-2-yl]oxy}cuprio)oxy]pent-3-en-2-one
• IUPAC Traditional name: 4-({[(4-oxopent-2-en-2-yl)oxy]cuprio}oxy)pent-3-en-2-one; (3E)-4-[({[(2E)-4-oxopent-2-en-2-yl]oxy}cuprio)oxy]pent-3-en-2-one
• Synonyms: Cu(acac)2; 2,4-Pentanedione copper(II) derivative; Bis(2,4-pentanedionato)copper(II); Cupric acetylacetonate; Copper(II) acetylacetonate; Bis(acetylacetonato)copper(II); Copper(II) 2,4-pentanedionate; 2,4-戊二酮 铜(II) 衍生物; 2,4-戊二酮铜(II); 乙酰丙酮铜; 乙酰丙酮酸铜; 乙酰丙酮铜(II)

Database IDs

• CAS Number: 13395-16-9
• EC Number: 236-477-9
• MDL Number: MFCD00000016
• Beilstein Number: 4157957
• PubChem SID: 24893105; 24882060; 24873754; 162244602
• PubChem CID: 5749883

CALCULATED PROPERTIES

• Acid pKa: 19.13614
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.0454
• LogD (pH = 7.4): -0.0454
• Log P: -0.0454
• Molar Refractivity: 54.8498 cm^3
• Polarizability: 23.55381 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder
• Melting Point: 284-288 °C (dec.)(lit.); ca 286°C dec.
• Boiling Point: 160°C/10mm

Safety Information

• RTECS: GL6520000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (KT); ≥99.99% trace metals basis; 97%; 98%
• Grade: purum
• Linear Formula: Cu(C5H7O2)2

DETAILS

Sigma Aldrich - 514365

Packaging
10, 50 g in poly bottle

Sigma Aldrich - C87851

Packaging
25, 100, 500 g in poly bottle

REFERENCES

• Catalyst for the carbenoid reaction of diazoacetate esters with silyl enol ethers to give siloxycyclopropanes: Liebigs Ann. Chem., 512 (1984); Org. Synth. Coll., 9, 573 (1998).
• In catalytic amounts promotes the selective O-benzylation of primary alcohols with benzyl chloride, in the presence of secondary alcohols or phenols: Tetrahedron Lett., 44, 8483 (2003). For a brief feature on uses of the reagent in synthesis, see: Synlett, 2859 (2005).
• The most effective of a number of metal chelates studied in enabling the reduction of aromatic nitro-compounds by sodium borohydride: J. Chem. Soc., Perkin 1, 2409 (1979).
• Promotes the coupling of organozinc reagents with allylic halides to give , δ-unsaturated esters: Tetrahedron Lett., 24, 2749 (1983).