Sodium acetylacetonate

Names
IUPAC name

Sodium (Z)-4-oxopent-2-en-2-olate

Identifiers

CAS Number

* 15435-71-9 Y

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

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[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]

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

|
|
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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
*[CID]: Compound ID
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