Sodium_acetylacetonate
Sodium acetylacetonate
Chemical compound
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]
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| IUPAC name
Sodium (Z)-4-oxopent-2-en-2-olate | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| 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).
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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
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.
The structure of the monohydrate has been established by X-ray crystallography. The sodium cation is bonded to the enolate oxygen centers.[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.
- Robert G. Charles (1959). "Tetraacetylethane". Organic Syntheses. 39: 61. doi:10.15227/orgsyn.039.0061.
- 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.