TROPONE 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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

TROPONE 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.

TROPONE(539-80-0)Related Product Information

• TROPONE
• Tropolone
• GLORIOSINE
• Colchicine
• TROPOLONE TOSYLATE
• DEMECOLCINE
• Hinokitiol
• colchiceine
• 5-Dibenzosuberenone
• 5-Bromo-2-methoxy-tropone
• Cycloheptatriene
• 2-CHLORO-2,4,6-CYCLOHEPTATRIEN-1-ONE
• TRIMETHYLCOLCHICINIC ACID
• 3,7-dihydroxytropolone
• trimethylcolchicinic acid methyl ether
• COLCHICINE, [RING C, METHOXY-3H]
• 2-methoxy-5-(2',3',4'-trimethoxyphenyl)tropone
• COLCHICINE SALICYLATED