Bis(dimethylamino)methane 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
CH3)2Nsub>2CH
2. It is classified as an
aminal as well as a di
tertiary amine
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 ...
, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reaction of
dimethylamine
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around ...
and
formaldehyde
Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
:
: 2 (CH
3)
2NH + CH
2O →
CH3)2Nsub>2CH
2 + H
2O
It is used for the dimethylaminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:
:
CH3)2Nsub>2CH
2 + H
+ → (CH
3)
2NCH
2+ + (CH
3)
2NH
Bis(dimethylamino)methane, being a
Lewis base, functions as a bidentate ligand.
[{{cite journal , doi=10.1002/chem.201600810 , title=Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That Can Be Trapped as Their [Mo(CO)4] Complexes , date=2016 , last1=Sharma , first1=Hemant K. , last2=Gonzalez , first2=Paulina E. , last3=Craig , first3=Alexander L. , last4=Chakrabarty , first4=Sanchita , last5=Metta-Magaña , first5=Alejandro , last6=Pannell , first6=Keith H. , journal=Chemistry – A European Journal , volume=22 , issue=22 , pages=7363–7366 , pmid=27111263 ]
Related reagents
*
N,N,N′,N′-Tetramethylformamidinium chloride
*
Eschenmoser's salt is used for similar applications.
References
Tertiary amines
Dimethylamino compounds