Sodium acetylacetonate

Sodium acetylacetonate
Names
	IUPAC name Sodium (Z)-4-oxopent-2-en-2-olate
Identifiers
CAS Number	15435-71-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	4588261;
PubChem CID	6008486;
	InChI 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;
	SMILES C/C(=C/C(=O)C)/[O-].[Na+];
Properties
Chemical formula	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

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]

Preparation[edit]

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[edit]

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[edit]

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

References[edit]

^ ^a ^b 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.
^ ^a ^b 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.

[Marilyn-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.

[Charles-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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