Triacetylmethane

Triacetylmethane
Names
	Other names 3-acetyl-2,4-pentanedione
Identifiers
CAS Number	815-68-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	63143;
EC Number	212-422-4;
PubChem CID	69950;
CompTox Dashboard (EPA)	DTXSID50231145 ;
	InChI InChI=1S/C7H10O3/c1-4(8)7(5(2)9)6(3)10/h7H,1-3H3 Key: AUZFRUHVDNDVJI-UHFFFAOYSA-N;
	SMILES CC(=O)C(C(=O)C)C(=O)C;
Properties
Chemical formula	C7H10O3
Molar mass	142.154 g·mol−1
Appearance	colorless liquid
Density	1.0591 g/cm3
Boiling point	96–97 °C (205–207 °F; 369–370 K) 15 torr
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264+P265, P280, P305+P351+P338, P337+P317
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Triacetylmethane is the organic compound with the formula HC(C(O)CH₃)₃. It is a colorless liquid that is soluble in organic solvents and in alkaline water. It readily forms an enolate.[2][3] The enolate forms a variety of metal complexes related to the metal acetylacetonates.[4]

References

"Triacetylmethane". pubchem.ncbi.nlm.nih.gov.
Arnett, Edward M.; Maroldo, Stephen G.; Schilling, Steven L.; Harrelson, John A. (1984). "Ion pairing and reactivity of enolate anions. 5. Thermodynamics of ionization of .beta.-di- and tricarbonyl compounds in dimethyl sulfoxide solution and ion pairing of their alkali salts". Journal of the American Chemical Society. 106 (22): 6759–6767. doi:10.1021/ja00334a049.
Yoshida, Z.; Ogoshi, H.; Tokumitsu, T. (1970). "Intramolecular Hydrogen Bond in Enol Form of 3-Substituted-2,4-Pentanedione". Tetrahedron. 26 (24): 5691–5697. doi:10.1016/0040-4020(70)80005-9.
Basato, Marino; Caneva, Elisabetta; Tubaro, Cristina; Veronese, Augusto Cesare (2009). "Coordinating Properties of the Anionic Ligand (MeCO)₂C(−)C(X)Me (X=O or NH) Toward Transition Metal(II) Centers". Inorganica Chimica Acta. 362 (8): 2551–2555. doi:10.1016/j.ica.2008.11.017.

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[1] "Triacetylmethane". pubchem.ncbi.nlm.nih.gov.

[2] Arnett, Edward M.; Maroldo, Stephen G.; Schilling, Steven L.; Harrelson, John A. (1984). "Ion pairing and reactivity of enolate anions. 5. Thermodynamics of ionization of .beta.-di- and tricarbonyl compounds in dimethyl sulfoxide solution and ion pairing of their alkali salts". Journal of the American Chemical Society. 106 (22): 6759–6767. doi:10.1021/ja00334a049.

[3] Yoshida, Z.; Ogoshi, H.; Tokumitsu, T. (1970). "Intramolecular Hydrogen Bond in Enol Form of 3-Substituted-2,4-Pentanedione". Tetrahedron. 26 (24): 5691–5697. doi:10.1016/0040-4020(70)80005-9.

[4] Basato, Marino; Caneva, Elisabetta; Tubaro, Cristina; Veronese, Augusto Cesare (2009). "Coordinating Properties of the Anionic Ligand (MeCO)₂C(−)C(X)Me (X=O or NH) Toward Transition Metal(II) Centers". Inorganica Chimica Acta. 362 (8): 2551–2555. doi:10.1016/j.ica.2008.11.017.