Dimethylbenzylamine
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| UN number | 2619 |
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| Appearance | colourless liquid |
| Density | 0.91 g/cm3 at 20 °C |
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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[2][3]
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:[4]
- [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.[5][6][7][8]
References
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