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Phorone

Catalog Number: EVT-1209685

CAS Number: 504-20-1

Molecular Formula: C9H14O
(CH3)2C=CHCOCH=C(CH3)2

C9H14O

Molecular Weight: 138.21 g/mol

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Product Introduction

Description

Phorone, also known as diisopropylidene acetone, is a yellow crystalline substance with a geranium odor. It has the chemical formula C9H14O or ((CH3)2C=CH)2C=O.

Synthesis Analysis

Phorone was first obtained in 1837 in impure form by the French chemist Auguste Laurent, who called it "camphoryle". 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". On both occasions, it was produced by ketonization through the dry distillation of the calcium salt of camphoric acid. Nowadays, it is 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. Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.

Molecular Structure Analysis

Phorone is an isoprenoid natural product and a constitutional isomer which bears the unprecedented tetracyclic phorane carbon skeleton.

Chemical Reactions Analysis

Phorone can condense with ammonia to form triacetone amine. The reactions of phorone with unsubstituted and monosubstituted cyclopentadienes proceeded rather rapidly due to the high reactivity of the latter.

Physical And Chemical Properties Analysis

Phorone has a molar mass of 138.210 g·mol−1. It appears as yellow crystals and has a geranium odor. It has a density of 0.885 g/cm3 . Its melting point is 28 °C (82 °F; 301 K) and boiling point is 198 to 199 °C (388 to 390 °F; 471 to 472 K).

Properties

CAS Number

504-20-1

Product Name

Phorone

IUPAC Name

2,6-dimethylhepta-2,5-dien-4-one

Molecular Formula

C9H14O
(CH3)2C=CHCOCH=C(CH3)2

C9H14O

Molecular Weight

138.21 g/mol

InChI

InChI=1S/C9H14O/c1-7(2)5-9(10)6-8(3)4/h5-6H,1-4H3

InChI Key

MTZWHHIREPJPTG-UHFFFAOYSA-N

SMILES

CC(=CC(=O)C=C(C)C)C

Solubility

Solubility in water: poo

Synonyms

Diisobutenyl Ketone; Diisopropylidene Acetone; Foron; NSC 38718; NSC 403517; Phorone; sym-Diisopropylidene Acetone; 2,6-Dimethyl-2,5-heptadien-4-one

Canonical SMILES

CC(=CC(=O)C=C(C)C)C

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