Dimethylbenzylamine is the
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
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
C
6H
5CH
2N(CH
3)
2. The molecule consists of a
benzyl
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group ().
Nomenclature
In IUPAC nomenclature, the prefix benzyl refers to a substituent ...
group, C
6H
5CH
2, attached to a dimethyl
amino
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
functional group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
. It is a colorless liquid. It is used as a catalyst for the formation of
polyurethane
Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...
foams and epoxy resins.
Synthesis
''N'',''N''-Dimethylbenzylamine can be synthesized by the
Eschweiler–Clarke reaction
The Eschweiler–Clarke reaction (also called the Eschweiler–Clarke methylation) is a chemical reaction whereby a primary (or secondary) amine is methylated using excess formic acid and formaldehyde. Reductive amination reactions such as this on ...
of
benzylamine
Benzylamine, also known as phenylmethylamine, is an Organic chemistry, organic chemical compound with the Structural formula#Condensed formulas, condensed structural formula C6H5CH2NH2 (sometimes abbreviated as Phenyl group#Nomenclature, PhCH2NH2 ...
Reactions
It undergoes
directed ortho metalation
Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho- position of a direct metalation group or DMG through the intermediary of an aryllithium co ...
with
butyl lithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis:
* ''n''-Butyllithium, abbreviated BuLi or nBuLi
* ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ...
:
:[C
6H
5CH
2N(CH
3)
2 + BuLi → 2-LiC
6H
4CH
2N(CH
3)
2
:LiC
6H
4CH
2N(CH
3)
2 + E
+ → 2-EC
6H
4CH
2N(CH
3)
2
Via these reactions, many derivatives are known with the formula 2-X-C
6H
4CH
2N(CH
3)
2 (E = SR, PR
2, etc.).
The amine is basic and undergoes quaternization with alkyl halides (e.g. hexyl bromide) to give quaternary ammonium salts:
:[C
6H
5CH
2N(CH
3)
2 + RX → [C
6H
5CH
2N(CH
3)
2R]
+X
−
Such salts are useful
phase transfer catalyst
In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the transition of a reactant from one phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of catalysis and can act through homog ...
s.
Uses
As the molecule has tertiary amine functionality, two of the key uses are as an epoxy-amine cure enhancement catalyst and also as a polyurethane catalyst.
References
External links
Safety MSDS data{{Webarchive, url=https://web.archive.org/web/20071011092357/http://ptcl.chem.ox.ac.uk/MSDS/DI/N,N-dimethylbenzylamine.html , date=2007-10-11
Dimethylamino compounds
Benzyl compounds