Phorone

Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula C₉H₁₄O or ((CH₃)₂C=CH)₂C=O.

Phorone

Names
Preferred IUPAC name 2,6-Dimethylhepta-2,5-dien-4-one
Other names Phorone Diisopropylidene acetone
Identifiers
CAS Number	504-20-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:35572
ChEMBL	ChEMBL2766015
ChemSpider	10007 Y
ECHA InfoCard	100.007.261
EC Number	207-986-3
PubChem CID	10438
RTECS number	MI5500000
UNII	8F20OEI0MV Y
UN number	1993
CompTox Dashboard (EPA)	DTXSID1021584
InChI InChI=1S/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3 N Key: MTZWHHIREPJPTG-UHFFFAOYSA-N N InChI=1/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3 Key: MTZWHHIREPJPTG-UHFFFAOYAY
SMILES O=C(C=C(C)C)C=C(C)C
Properties
Chemical formula	((CH3)2C=CH)2C=O
Molar mass	138.210 g·mol−1
Appearance	Yellow crystals
Odor	Geranium
Density	0.885 g/cm3
Melting point	28 °C (82 °F; 301 K)
Boiling point	198 to 199 °C (388 to 390 °F; 471 to 472 K)
Hazards
Flash point	79 °C (174 °F; 352 K)
Safety data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation

It was first obtained in 1837 in impure form by the French chemist Auguste Laurent, who called it "camphoryle".^[1] In 1849, the French chemist Charles Frédéric Gerhardt and his student Jean Pierre Liès-Bodart prepared it in a pure state and named it "phorone".^[2] On both occasions it was produced by ketonization through the dry distillation of the calcium salt of camphoric acid.^[3][4]

CaC₁₀H₁₄O₄ → C₉H₁₄O + CaCO₃

It is now typically obtained by the acid-catalysed twofold aldol condensation of three molecules of acetone. Mesityl oxide is obtained as an intermediate and can be isolated.^[5]

Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.

Reactions

Phorone can condense with ammonia to form triacetone amine.

See also

• Isophorone