9-Bromophenanthrene

Description

9-Bromophenanthrene is a luminescent material that fluoresces at short wavelengths and can be used as a molecular probe to detect the presence of other compounds and the mechanism of reaction, among other things.

Chemical properties

light yellow powder. soluble in toluene, and chloroform (50 mg/ml).

The Uses of 9-Bromophenanthrene

9-Bromophenanthrene is used as halogenated building block. Isotope labelled 9-Bromophenanthrene (B687200), a halogenated polycyclic aromatic hydrocarbon that has been seen to have a room temperature phosphorescence that can be induced by β-cyclodextrin (β-CD) in the presence of cyclohexane; however, trace Fe(III) causes a decrease of the RTP emission.

Preparation

9-Bromophenanthrene (90-94%) is produced by adding bromine to a refluxing solution of phenanthrene in carbon tetrachloride. This is the starting-point of 9-substituted phenanthrenes, e.g, when heated with cuprous cyanide at 260℃, 9-bromophenanthrene forms the corresponding cyano-compound; this may be hydrolysed to phenanthrene-9-carboxylic acid. Phenanthrene undergoes the Friedel-Crafts reaction mainly in the 3-, and to a small extent, in the 2-position. It is chloromethylated in the 9-position. When nitrated, phenanthrene gives a mixture of three mononitro-derivatives, the 3-isomer predominating. Sulphonation of phenanthrene gives a mixture of 1-, 2-, 3- and 9-phenanthrenesulphonic acids, and the ratio of these isomers depends on the temperature.