Sodium acetylacetonate

Sodium acetylacetonate
Names
IUPAC name
Sodium (Z)-4-oxopent-2-en-2-olate
Identifiers
CAS Number
  • 15435-71-9 checkY
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
  • 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
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]

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. ^ 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.
  2. ^ a b 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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Metal acetylacetonate complexes
H(acac) He
Li Be B C N O F Ne
Na(acac) Mg Al(acac)3 Si P S Cl Ar
K Ca Sc(acac)3 Ti(acac)2Cl2
Ti(acac)3 		V(acac)3
VO(acac)2 		Cr(acac)2
Cr(acac)3 		Mn Fe(acac)2
Fe(acac)3 		Co(acac)2
Co(acac)3 		[Ni(acac)2]3 Cu(acac)2 Zn(acac)2 Ga(acac)3 Ge As Se Br Kr
Rb Sr Y(acac)3 Zr(acac)4 Nb MoO2(acac)2 Tc Ru(acac)3 Rh(acac)(CO)2
Rh(acac)3 		Pd(acac)2 Ag Cd In(acac)3 Sn Sb Te I Xe
Cs Ba(acac)2 * Lu(acac)3 Hf(acac)4 Ta W Re Os Ir(acac)3 Pt(acac)2 Au Hg Tl(acac) Pb Bi Po At Rn
Fr Ra ** Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* La(acac)3 Ce(acac)3 Pr(acac)3 Nd(acac)3 Pm Sm(acac)3 Eu(fod)3
Eu(acac)3 		Gd(acac)3 Tb(acac)3 Dy(acac)3 Ho(acac)3 Er(acac)3 Tm(acac)3 Yb(acac)3
** Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No