Sodium acetylacetonate

Sodium acetylacetonate is an organic compound with the nominal formula Na[CH(C(O)CH3)2]. This white, water-soluble solid is the conjugate base of acetylacetone.[1]

Sodium acetylacetonate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H8O2.Na/c1-4(6)3-5(2)7;/h3,6H,1-2H3;/q;+1/p-1/b4-3-;
    Key: AIWZOHBYSFSQGV-LNKPDPKZSA-M
  • C/C(=C/C(=O)C)/[O-].[Na+]
Properties
C5H7NaO2
Molar mass 122.099 g·mol−1
Appearance white solid
Melting point 210 °C (410 °F; 483 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

The compound is prepared by deprotonation of acetylacetone: [2]

NaOH + CH2(C(O)CH3)2 → NaCH(C(O)CH3)2 + H2O

The anhydrous compound is produced by deprotonation with sodium hydride in an aprotic solvent such as THF:[3]

NaH + CH2(C(O)CH3)2 → NaCH(C(O)CH3)2 + H2

Reactions

Oxidation of the salt gives tetraacetylethane.[2]

With metal salts, it reacts to give metal acetylacetonate complexes.

Alkylation of sodium acetylacetonate can result in both O-alkylation and C-alkylation. The former gives the enol ether and the latter gives 3-substituted derivative of acetylacetone.

Structure

The structure of the monohydrate has been established by X-ray crystallography. The sodium cation is bonded to the enolate oxygen centers.[1]

References
  1. Sahbari, J. J.; Olmstead, M. M. (1983). "Structure of Sodium Acetylacetonate Monohydrate, Na[C5H7O2].H2O". Acta Crystallographica Section C Crystal Structure Communications. 39 (8): 1037–1038. doi:10.1107/S0108270183007283.
  2. Robert G. Charles (1959). "Tetraacetylethane". Organic Syntheses. 39: 61. doi:10.15227/orgsyn.039.0061.
  3. Krafft, Marie E.; Procter, Martin J.; Abboud, Khalil A. (1999). "Synthesis of Molybdenum Dicarbonyl Complexes Bearing Tethered Homoallylic Amines and Sulfides". Organometallics. 18 (7): 1122–1124. doi:10.1021/OM9807102.
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