Nickel(II) 2,4-pentanedionate

• Catalog No.: 18811
• CAS Number: 3264-82-2
• M. F.: C10H14NiO4
• M. W.: 256.90916
• Purity: 95%

SYNONYMS

• Title: 乙酰丙酮镍(II)
• IUPAC name: (3Z)-4-[({[(2Z)-4-oxopent-2-en-2-yl]oxy}nickelio)oxy]pent-3-en-2-one
• IUPAC Traditional name: (3Z)-4-[({[(2Z)-4-oxopent-2-en-2-yl]oxy}nickelio)oxy]pent-3-en-2-one
• Synonyms: Bis(acetylacetonato)nickel(II); Nickel(II) acetylacetonate

DATABASE IDS

• MDL Number: MFCD00000024
• Merck Index: 146500
• Beilstein Number: 4157970
• EC Number: 221-875-7
• CAS Number: 3264-82-2

PROPERTIES

• Purity: 95%
• Apperance: Powder
• Melting Point: ca 230°C dec.
• Solubility: Soluble in water, alcohol, toluene
• GHS Hazard statements: H350-H302-H317
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P201-P308+P313
• Risk Statements: 49-22-43
• RTECS: SA2100000
• Safety Statements: 53-45
• Storage Warning: Hygroscopic
• TSCA Listed: 是

REFERENCES

• Catalyst for a variety of coupling reactions, e.g.: Coupling of Grignard reagents to give biaryls: J. Org. Chem., 41, 2252 (1976). Coupling of Grignards with silyl enol ethers of both aldehydes and ketones, to give alkenes. In contrast to Dichlorobis(triphenylphosphine)nickel(II), 13930, this reagent gives the thermodynamically more stable alkene: Tetrahedron Lett., 3915 (1980). Cross-coupling of alkyl iodides with dialkylzinc reagents tolerates a variety of functionalities: Angew. Chem. Int. Ed., 34, 2723 (1995).
• Aryl phosphates couple with Grignards (aryl tosylates do not couple under these conditions), affording high yields of biaryls: Tetrahedron Lett., 22, 4449 (1981). Cross-coupling of aryl chlorides with arylzincs also yields biaryls: Tetrahedron Lett., 39, 6441, 7275 (1998).
• For use in the condensation of active methylene compounds with lactims, see Isopropylidene malonate, A15603.
• Catalyst for the conjugate addition of 1,3-dicarbonyl compounds to various Michael acceptors: J. Org. Chem., 45, 1246 (1980).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1042 (2005).