Dimethylbenzylamine is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with the
formula 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 () group.
Nomenclature
In IUPAC nomenclature, the prefix benzyl refers to a subst ...
group, C
6H
5CH
2, attached to a dimethyl
amino
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent su ...
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...
. It is a colorless liquid. It is used as a catalyst for the formation of
polyurethane
Polyurethane (; often abbreviated PUR and PU) refers to 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, polyurethan ...
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 is an organic chemical compound with the condensed structural formula C6H5CH2NH2 (sometimes abbreviated as PhCH2NH2 or BnNH2). It consists of a benzyl group, C6H5CH2, attached to an amine functional group, NH2. This colorless wate ...
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:
[{{cite journal, title=o-Methylethylbenzyl Alcohol, authors=W. R. Brasen, C. R. Hauser, journal=Org. Synth., year=1954, volume=34, page=58, doi=10.15227/orgsyn.034.0058]
:
6H5CH2N(CH3)2 + RX → [C6H5CH2N(CH3)2Rsup>+X
−
Such salts are useful phase transfer catalysts.
References
External links
Safety MSDS data
Alkyl-substituted benzenes
Dimethylamino compounds
Benzyl compounds