TROPONE

Product NameTROPONE
CAS539-80-0
MFC7H6O
MW106.12
EINECS208-725-6
MOL File539-80-0.mol

Chemical Properties

Melting point	-7°C
Boiling point	113 °C/15 mmHg (lit.)
Density	1.094 g/mL at 25 °C (lit.)
refractive index	n20/D 1.615(lit.)
Flash point	>110°C
storage temp.	-20°C
solubility	sol ether, dioxane, acetone, benzene, toluene, xylene, MeCN, CCl4; miscible with water.
form	Liquid
color	very deep brown
BRN	1902335

Safety Information

Safety Statements	24/25
WGK Germany	3
F	10-23

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Uses

Tropone has been used in synthesis of:

bicyclic δ-lactones via heterocyclic carbine-catalyzed [8+3] annulation pathway
6,7-benzobicyclo [3.2.2] nona-3,6,8-trien-2-one via thermal addition to bezyne

Application

Tropone can be used to prepare the synthon of cycloheptadiene-1-one; it is used as the basis for the synthesis of cycloheptadiene compounds, fluorene compounds, polycyclic compounds, and natural products.

Preparation

2,4,6-cycloheptatrien-1-one (1) is a functionalized conjugated carbocyclic compound with diversified reactivity. The most popular and simple method of preparation involves oxidation of 1,3,5- Cycloheptatriene with Selenium(IV) Oxide-KH2PO4. Several other procedures have also been developed, among which electrooxidation of cycloheptatrienes and α-pyrone ring expansion via high-pressure cycloaddition of cyclopropenone acetals can be considered general methods of synthesis of tropones.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 5442, 1956 DOI: 10.1021/ja01601a077
The Journal of Organic Chemistry, 29, p. 960, 1964
Organic Syntheses, Coll. Vol. 9, p. 396, 1998

General Description

Metal-catalyzed [6+3] cycloaddition of tropone with azomethine ylides has been reported.