Sodium acetylacetonate
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IUPAC name Sodium (Z)-4-oxopent-2-en-2-olate | |
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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
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
- ^ 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.
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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 |