1,3,5-Tribromobenzene is an
aryl bromide and isomer of
tribromobenzene, also known as ''sym''-tribromobenzene.
Preparation
Brominating
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polyme ...
aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine
In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...
with elemental
bromine
Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simila ...
gives
2,4,6-tribromoaniline. This is then
diazotized, then reacted with
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
to replace the
diazonium group with hydrogen, forming 1,3,5-tribromobenzene.
It has also been prepared by these methods:
* replacement of the amino group of
3,5-dibromoaniline with bromine
* the action of light on
bromoacetylene, effecting an
alkyne trimerisation
In organic chemistry, an alkyne trimerisation is a +2+2nbsp; cycloaddition reaction in which three alkyne units () react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applic ...
to 1,3,5-tribromobenzene
* decomposition of
2,4,6-tribromophenylhydrazine
* reduction of
2,4,6-tribromobenzenediazonium sulfate
* a side product in the preparation of
2,4,6-tribromobenzonitrile
Reactions and uses
1,3,5-Tribromobenzene is a precursor to C
3-symmetric molecules. It undergoes a
Suzuki reaction with three equivalents of
4-formylphenylboronic acid to form
1,3,5-tris(4-formylphenyl)benzene (TFPB), a monomer for
covalent organic framework
Covalent organic frameworks (COFs) are a class of materials that form two- or three-dimensional structures through reactions between organic precursors resulting in strong, covalent bonds to afford porous, stable, and crystalline materials. COFs em ...
s.
References
{{DEFAULTSORT:Tribromobenzene, 1,3,5-
Bromobenzenes