Glyoxal-bis(mesitylimine) is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula H
2C
2(NC
6H
2Me
3)
2 (Me =
methyl
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
). It is a yellow solid that is soluble in organic solvents. It is classified as a
diimine
Diimines are organic compounds containing two imine (RCH=NR') groups. Common derivatives are 1,2-diimines and 1,3-diimines. These compounds are used as ligands, but they are also precursors to other organic compounds.
Preparation
Diimines are ...
ligand
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...
. It is used in
coordination chemistry
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...
and
homogeneous catalysis
In chemistry, homogeneous catalysis is catalysis where the catalyst is in same phase as reactants, principally by a soluble catalyst in a solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in d ...
. It is synthesized by condensation of
2,4,6-trimethylaniline
2,4,6-Trimethylaniline is an organic compound with formula (CH3)3C6H2NH2. It is an aromatic amine that is of commercial interest as a precursor to dyes. It is prepared by selective nitration of mesitylene, avoiding oxidation of the methyl groups, ...
and
glyoxal
Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...
. In addition to its direct use as a ligand, it is a precursor to imidazole precursors to the popular
NHC ligand
A persistent carbene (also known as stable carbene) is an organic molecule whose natural resonance structure has a carbon atom with incomplete octet (a carbene), but does not exhibit the tremendous instability typically associated with such moiet ...
called
IMes
IMes is an abbreviation for an organic compound that is a common ligand in organometallic chemistry. It is an ''N''-heterocyclic carbene (NHC). The compound, a white solid, is often not isolated but instead is generated upon attachment to the me ...
.
Related compounds
*Glyoxal-bis(triisopropylphenylimine), which is bulkier than glyoxal-bis(mesitylimine).
[{{cite journal, title=Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix, first1=Junting, last1=Chen, first2=Tobias, last2=Ritter, journal=Org. Synth. , year=2019, volume=96, page=16, doi=10.15227/orgsyn.096.0016, doi-access=free]
References
Chelating agents
Imines