9-Fluorenone

Description

9-fluorenone is an important intermediate for organic synthesis. It can be used to manufacture a variety of fine chemicals, mainly used as a modifier for the production of polymer materials, bisphenol fluorene, fluorenyl benzoxazine resin, acrylic resin, polyester, polycarbonate and epoxy resin. In the laboratory, fluorene was used as the raw material, dimethyl sulfoxide as the solvent, sodium hydroxide as the catalyst and oxygen as the oxidant. The oxidizing reaction was carried out by a tower packing reactor. The reaction solution was cooled and filtered to obtain a crude fluorenone. The content of crude fluorenone is 93%. We can recover 94% of the solvent and part of the crude fluorenone through distillation of the filtrate. The crude fluorenone is purified by directional crystallization to obtain yellow flaky fluorenone that have a purity of 99.8% or more.

Chemical properties

yellow flakes, chips or crystalline powder; Soluble in ethanol and ether, insoluble in water.

The Uses of 9-Fluorenone

9-Fluorenone is used in the preparation of antimalarial drugs. It is a fluorene derivative. Further, it is used in functional polymer and in dyes.

What are the applications of Application

9-Fluorenone is 9-Fluorenone is a polycyclic aromatic ketone that has photosensitizing properties and also has the ability to undergo electrochemical polymerization. 9-Fluorenone is used in industry as an initiator in visible-light cured resin systems. 9-Fluorenone has potentially toxic effects on humans, as exposure can cause DNA mutations.

Definition

ChEBI: Fluoren-9-one is the simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9. It has a role as a fungal xenobiotic metabolite.

What are the applications of Application

9-Fluorenone has been extensively used as a precursor to synthesize a variety of organic electronic materials. Some of the general examples are:
Synthesis of host for the blue and green phosphorescent organic light emitting diodes (PHOLEDs).
Synthesis of fluorene-based molecular motors.
Synthesis of open-shell Chichibabin′s hydrocarbons as potential organic spintronic materials.
It also acts as a sensitizer in the formation of picene via photosensitization of 1,2-di(1-naphthyl)ethane.

Preparation

Fluorenone can be produced by catalytic oxidation of fluorene, or of fluorene fractions in the presence of a quarternary ammonium salt, or by catalytic oxidative cracking (oxicracking) of a suitable aromatic.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 3934, 1995 DOI: 10.1021/jo00118a002
Synthetic Communications, 6, p. 285, 1976 DOI: 10.1080/00397917608063524

Purification Methods

Crystallise 9-fluorenone from absolute EtOH, MeOH or *benzene/pentane. [Ikezawa J Am Chem Soc 108 1589 1986.] Also recrystallise it twice from toluene and sublime it in a vacuum [Saltiel J Am Chem Soc 108 2674 1986]. It can be distilled under high vacuum. [Beilstein 7 H 465, 7 III 2330, 7 IV 1629.]