Dimethylbenzylamine
Appearance
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Names | |||
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Preferred IUPAC name
N,N-Dimethyl-1-phenylmethanamine | |||
Other names
N,N-Dimethylbenzenemethanamine, N,N-Dimethylbenzylamine, N-Benzyldimethylamine, Dimethylbenzylamine, Benzyl-N,N-dimethylamine, N-(Phenylmethyl)dimethylamine, BDMA, Sumine 2015, Benzenemethanamine, Dabco B-16, Araldite accelerator 062, N,N-Dimethyl(phenyl)methanamine, DMBA[1]
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Identifiers | |||
3D model (JSmol)
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ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.002.863 | ||
EC Number |
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PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C9H13N | |||
Molar mass | 135.210 g·mol−1 | ||
Appearance | colourless liquid | ||
Density | 0.91 g/cm3 at 20 °C | ||
Melting point | −75 °C (−103 °F; 198 K) | ||
Boiling point | 180 to 183 °C (356 to 361 °F; 453 to 456 K) | ||
1.2 g/100mL | |||
Hazards | |||
NFPA 704 (fire diamond) | |||
Flash point | 55 °C (131 °F; 328 K) | ||
410 °C (770 °F; 683 K) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
References
- ^ "N,N-dimethyl benzyl amine". The Good Scents Company. Retrieved 1 November 2020.
- ^ Icke, R. N.; Wisegarver, B. B.; Alles, G. A. (1945). "β-Phenylethyldimethylamine". Organic Syntheses. 25: 89. doi:10.15227/orgsyn.025.0089.
- ^ 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.
- ^ "o-Methylethylbenzyl Alcohol". Org. Synth. 34: 58. 1954. doi:10.15227/orgsyn.034.0058.
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