Names | |
---|---|
Preferred IUPAC name
2,6-Dimethylhepta-2,5-dien-4-one | |
Other names
Phorone
Diisopropylidene acetone | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.261 |
EC Number |
|
PubChem
CID
|
|
RTECS number |
|
UNII | |
UN number | 1993 |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
((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).
|
Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula C9H14O or ((CH3)2C=CH)2C=O.
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]
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.
Phorone can condense with ammonia to form triacetone amine.
Names | |
---|---|
Preferred IUPAC name
2,6-Dimethylhepta-2,5-dien-4-one | |
Other names
Phorone
Diisopropylidene acetone | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.261 |
EC Number |
|
PubChem
CID
|
|
RTECS number |
|
UNII | |
UN number | 1993 |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
((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).
|
Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula C9H14O or ((CH3)2C=CH)2C=O.
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]
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.
Phorone can condense with ammonia to form triacetone amine.