3264-82-2 Usage
Description
Bis(2,4-pentanediono)nickel, also known as Nickel(II) acetylacetonate, is an organonickel compound with the chemical formula Ni(CH3COCHCOCH3)2. It is characterized by its emerald-green crystalline appearance and an orthorhombic structure. Bis(2,4-pentanediono)nickel is known for its solubility in various organic solvents and has a density of 1.455 g/cm3 at 17°C, melting point at 230°C, and is insoluble in ether.
Uses
1. Used in Catalyst Applications:
Bis(2,4-pentanediono)nickel is used as a catalyst in hydrogenation and other organic reactions, playing a crucial role in facilitating chemical transformations.
2. Used in Grignard Synthesis:
In the field of organic chemistry, Nickel(II) acetylacetonate is utilized in the Grignard synthesis of nickelocene from cyclopentadienyl magnesium halides. Its solubility in organic solvents makes it a valuable component in this process.
3. Used in Organometallic Compounds Synthesis:
Bis(2,4-pentanediono)nickel is employed in the preparation of organometallic compounds such as nickelocene and bis(cyclooctadiene) nickel, which are important in various chemical applications.
4. Used in Polymer and Resin Preparation:
Nickel Acetylacetonate is used in the preparation method of Bisphenol Dipropargyl Ether and Cyanate Ester blending resin, contributing to the development of new materials with specific properties for various industries.
5. Used in Industrial Catalysis:
Bis(2,4-pentanediono)nickel is also industrially significant as a catalyst component in the oligomerization of alkenes and in the conversion of acetylene to cyclooctatetraene, contributing to the production of valuable chemicals and materials.
Preparation
Nickel 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
Preparation
Nickel(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.
Flammability and Explosibility
Notclassified
Safety Profile
Confirmed human carcinogen. Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.
Purification Methods
Wash 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 3264-82-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,6 and 4 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3264-82:
(6*3)+(5*2)+(4*6)+(3*4)+(2*8)+(1*2)=82
82 % 10 = 2
So 3264-82-2 is a valid CAS Registry Number.
InChI:InChI=1/2C5H8O2.Ni/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b2*4-3-;
3264-82-2Relevant articles and documents
Ferbinteanu, Marilena,Andruh, Marius,Segal, E.
, p. 241 - 248 (1991)
Nickel nanoparticles supported on MOF-5: Synthesis and catalytic hydrogenation properties
Zhao, Huahua,Song, Huanling,Chou, Lingjun
, p. 261 - 265 (2012/03/13)
Nickel nanoparticles (2-6 nm) were successfully deposited on MOF-5 (Zn 4O(BDC)3, BDC = 1,4-benzenedicarboxylate) by a facile wet impregnation strategy to prepare Ni@MOF-5 employing Ni(acac)2 (acac = acetylacetonate) as the precursor in absolute ethanol solvent owing to the sensitivity to the moisture of MOF-5. Ni@MOF-5 exhibited excellent catalytic activity for hydrogenation of C = C bond using crotonaldehyde as a probe molecule under mild reaction conditions (conversion > 90.0%, selectivity > 98.0%, 2.0 MPa, 100 °C, 40 min). In addition, the catalyst could be reused and the structure of MOF-5 framework was still maintained. Therefore, MOF-5 promised a novel candidate of support for hydrogenation catalyst.
Ni(acac)2/phosphine as an excellent precursor of nickel(0) for catalytic systems
Ananikov, Valentine P.,Gayduk, Konstantin A.,Starikova, Zoya A.,Beletskaya, Irina P.
, p. 5098 - 5102 (2011/01/05)
The coordination of phosphine ligands to nickel acetylacetonate was studied in toluene solution, and the first X-ray structure of the unstable complex trans-[Ni(acac)2(PMe2Ph)2] has been reported. A convenient procedure was developed to generate Ni(0) species in situ in solution from a Ni(acac)2 precursor, and their application in catalysis was demonstrated. A study of the reaction mechanism has suggested that water may play an important role in the formation of zerovalent nickel species. The nature of the Ni(0) species was confirmed by trapping with Ph 2S2, and the structure of the resulting complexes trans-[Ni(SPh)2L2] was established by X-ray analysis for L = PMe2Ph, PMePh2, PBu3.