• Source: Dimethylbenzylamine

Dimethylbenzylamine is the organic compound with the formula C6H5CH2N(CH3)2. The molecule consists of a benzyl group, C6H5CH2, attached to a dimethylamino functional group. It is a colorless liquid. It is used as a catalyst for the formation of polyurethane foams and epoxy resins.




Synthesis


N,N-Dimethylbenzylamine can be synthesized by the Eschweiler–Clarke reaction of benzylamine




Reactions


It undergoes directed ortho metalation with butyl lithium:

[C6H5CH2N(CH3)2 + BuLi → 2-LiC6H4CH2N(CH3)2
LiC6H4CH2N(CH3)2 + E+ → 2-EC6H4CH2N(CH3)2
Via these reactions, many derivatives are known with the formula 2-X-C6H4CH2N(CH3)2 (E = SR, PR2, etc.).
The amine is basic and undergoes quaternization with alkyl halides (e.g. hexyl bromide) to give quaternary ammonium salts:

[C6H5CH2N(CH3)2 + RX → [C6H5CH2N(CH3)2R]+X−
Such salts are useful phase transfer catalysts.




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 Archived 2007-10-11 at the Wayback Machine

Kata Kunci Pencarian:

• Dimethylbenzylamine
• Benzalkonium chloride
• C9H13N
• Accelerator
• Sommelet–Hauser rearrangement
• Charles R. Hauser
• Carbon–hydrogen bond activation