Dimethylbenzylamine

Dimethylbenzylamine

Dimethylbenzylamine

Chemical compound

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.

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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

  1. [1]
    "N,N-dimethyl benzyl amine". The Good Scents Company. Retrieved 1 November 2020.
  2. [2]
    Icke, R. N.; Wisegarver, B. B.; Alles, G. A. (1945). "β-Phenylethyldimethylamine". Organic Syntheses. 25: 89. doi:10.15227/orgsyn.025.0089.
  3. [3]
    Clarke, H. T.; Gillespie, H. B.; Weisshaus, S. Z. (1933). "The Action of Formaldehyde on Amines and Amino Acids". J. Am. Chem. Soc. 55 (11): 4571. doi:10.1021/ja01338a041.
  4. [4]
    W. R. Brasen; C. R. Hauser (1954). "o-Methylethylbenzyl Alcohol". Org. Synth. 34: 58. doi:10.15227/orgsyn.034.0058.
  5. [5]
    Firouzmanesh, Mr; Azar, A Aref (June 2003). "Study of the effect of BDMA catalyst in the epoxy novolac curing process by isothermal DSC". Polymer International. 52 (6): 932–937. doi:10.1002/pi.1135. ISSN 0959-8103.
  6. [6]
    Firouzmanesh, M. R.; Azar, A. Aref (March 2005). "Study of the Effect of BDMA Catalyst in Epoxy Novolac Curing Process by Isothermal DSC". Journal of Reinforced Plastics and Composites. 24 (4): 345–353. Bibcode:2005JRPC...24..345F. doi:10.1177/0731684405033953. ISSN 0731-6844. S2CID 93979685.
  7. [7]
    Zhang, Qian; Hu, Xiang-Ming; Wu, Ming-Yue; Zhao, Yan-Yun; Yu, Chuang (2018-07-15). "Effects of different catalysts on the structure and properties of polyurethane/water glass grouting materials". Journal of Applied Polymer Science. 135 (27): 46460. doi:10.1002/app.46460.
  8. [8]
    Mascorro, José A. (2003). "Benzyldimethylamine (BDMA): Catalyst of Choice with Epoxy Embedding Media". Microscopy Today. 11 (4): 47. doi:10.1017/s1551929500053104.
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