Fluorene

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Structural formula
Structural formula of fluorene
General
Surname Fluorene
other names
  • Diphenylene methane
  • 9 H fluorene
  • o -Biphenylmethane
  • 2,2'-methylenebiphenyl
  • 2,3-benzidene
  • FLO
Molecular formula C 13 H 10
Brief description

colorless leaflets

External identifiers / databases
CAS number 86-73-7
EC number 201-695-5
ECHA InfoCard 100.001.541
PubChem 6853
Wikidata Q417934
properties
Molar mass 166.22 g · mol -1
Physical state

firmly

density

1.2 g cm −3

Melting point

113-115 ° C

boiling point

295 ° C

solubility
safety instructions
GHS labeling of hazardous substances
09 - Dangerous for the environment

Caution

H and P phrases H: 410
P: 273-501
Toxicological data

16000 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fluorene is a chemical compound that belongs to the group of polycyclic aromatic hydrocarbons (PAHs). Fluoren glows violet when exposed to UV light , which is what gave the compound its name (see also: fluorescence ).

Occurrence

Fluorene occurs naturally as the very rare mineral kratochvílite .

Extraction and presentation

Fluorene is technically obtained from coal tar , namely from the washing oil fraction during the distillation of the tar. The substance is also produced in small quantities in addition to other aromatic polycyclic compounds when organic material is heated or burned in a lack of oxygen, and in traces also when petrol and diesel are burned.

properties

A special feature of fluorene is that it produces an aromatic anion when it is deprotonated . This is similar to the cyclopentadienyl anion . The fluorenyl anion is used as a ligand in organometallic chemistry , analogous to the cyclopentadienyl and indenyl anions . The group fluorenylmethoxycarbonyl (Fmoc), which is easy to deprotonate because of the property mentioned, serves as a basic protective group in chemical peptide synthesis .

use

Fluorene is used in the manufacture of dyes and plastics, as well as pesticides . Polyfluorene is widely used as a luminophore in organic light-emitting diodes . Fluorene and some of its derivatives act as mitogens ; that is, they initiate cell division. This explains the possible use of fluorene and fluorene carboxylic acids as plant growth substances . In medicine, non-toxic fluorene derivatives (e.g. fluorenone ) are discussed as a drug to increase tissue formation after transplants (see web link).

Individual evidence

  1. ↑ a b entry on fluorene. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
  2. ↑ a b c d e f Entry for CAS no. 86-73-7 in the GESTIS substance database of the IFA , accessed on December 14, 2012(JavaScript required) .
  3. ↑ European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, p. 605, ISBN 978-3-7692-3962-1 .
  4. ↑ Fluoren data sheet at AlfaAesar, accessed on December 15, 2010 ( PDF )(JavaScript required) .

Web links