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Nickel(II) acetylacetonate

Basic information Physical Properties Uses Preparation Safety Related Supplier
Nickel(II) acetylacetonate Basic information
Nickel(II) acetylacetonate Chemical Properties
  • Melting point:230 °C (dec.)(lit.)
  • Boiling point:220 °C (11 mmHg)
  • Density 0,145 g/cm3
  • vapor pressure 2.7 hPa (110 °C)
  • refractive index 1.57-1.64
  • Flash point:>200°C
  • storage temp. Store below +30°C.
  • solubility 4.8g/l
  • form Liquid
  • color Clear pale yellow
  • Specific Gravity1.455
  • Water Solubility soluble
  • Sensitive Hygroscopic
  • Hydrolytic Sensitivity0: forms stable aqueous solutions
  • Merck 14,6500
  • BRN 4157970
  • Stability:hygroscopic
  • InChIKeyYAGMVFMEBGIOTO-FGSKAQBVSA-M
  • CAS DataBase Reference3264-82-2
  • NIST Chemistry ReferenceNickel acetylacetonate(3264-82-2)
  • EPA Substance Registry SystemNickel, bis(2,4-pentanedionato-.kappa.O,.kappa.O')-, (SP-4-1)- (3264-82-2)
Safety Information
  • Hazard Codes T,Xi,Xn
  • Risk Statements 49-22-43-40
  • Safety Statements 53-36/37/39-45-36/37
  • WGK Germany 3
  • RTECS SA2100000
  • TSCA Yes
  • HS Code 29420000
  • ToxicityLD50 orally in Rabbit: 587 mg/kg
MSDS
Nickel(II) acetylacetonate Usage And Synthesis
  • Physical PropertiesEmerald-green crystals; orthorhombic structure; density 1.455 g/cm3 at 17°C; melts at 230°C; soluble in water, alcohol, chloroform, benzene and toluene; insoluble in ether.
  • UsesBis(2,4-pentanediono)nickel is used as a catalyst in hydrogenation and other organic reactions.
  • PreparationNickel acetylacetonate is prepared by the reaction of acetylacetone with nickel chloride hexahydrate or nickel hydroxide, followed by crystallization:
    2CH3C(=O)CH2C(=O)CH3 + Ni(OH)2 → Ni(CH3C(=O)CHC(=O)CH3)2 + 2H2O
  • Chemical PropertiesNickel(II) acetylacetonate Ni(CH3COCHCOCH3)2, is obtained as emerald green crystals by dehydration of the dihydrate at 50°C in vacuum; it has an unusual trimeric structure in the solid state. The dihydrate Ni(CH3COCH3)2.2H2O is prepared by the addition of acetylacetone to solutions of nickel(II) salts in the presence of a weak base such as sodium acetate. Nickel(II) acetylacetonate is soluble in organic solvents and finds use in the synthesis of organometallic compounds such as nickelocene and bis(cyclooctadiene) nickel. It is also industrially important as a catalyst component in the oligomerization of alkenes and in the conversion of acetylene to cyclooctatetraene.
  • UsesCatalyst for organic reactions.
  • UsesNickel(II) acetylacetonate is usefully soluble in organic solvents and is therefore used in the Grignard synthesis of nickelocene from cyclopentadienyl magnesium halides. More ionic nickel(II) salts such as the thiocyanate can be reacted with potassium cyclopentadienide in liquid ammonia.
  • PreparationNickel(II) acetylacetonate is isolated as the dihydrate Ni(acac)2·2H2O from aqueous solutions of nickel(II) salts in the presence of acetylacetone and a weak base such as sodium acetate; it is readily dehydrated to the green anhydrous compound at 50° in vacuo. From ammoniacal solutions of nickel(II) salts the diammoniate Ni(acac)2·2NH3 precipitates; this also readily evolves the two extra ligands to give the green acetylacetonate.
  • Safety ProfileConfirmed human carcinogen. Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Purification MethodsWash the green solid with H2O, dry it in a vacuum desiccator and recrystallise it from MeOH. [Charles & Pawlikowski J Phys Chem 62 440 1958.] The complex can be conveniently dehydrated by azeotropic distillation with toluene, and the crystals may be isolated by concentrating the toluene solution. [Wilkinson et al. J Am Chem Soc 76 1970 1954, Beilstein 1 IV 3677.]
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