ChemicalBook CAS DataBase List 9-Bromophenanthrene

9-Bromophenanthrene synthesis

7synthesis methods

Product Name:9-Bromophenanthrene
CAS Number:573-17-1
Molecular formula:C14H9Br
Molecular Weight:257.13

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.

91-20-3 Synthesis

91-20-3
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573-17-1
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Yield:-

Steps:

Multi-step reaction with 4 steps
1: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
2: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
3: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
4: N-Bromosuccinimide; gold(III) chloride / 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere

References:

Murai, Masahito;Ogita, Takuya;Takai, Kazuhiko [Chemical Communications,2019,vol. 55,# 16,p. 2332 - 2335]