Dimethylbenzylamine

Dimethylbenzylamine
Names
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
Identifiers
103-83-3 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL45591 YesY
ChemSpider 7398 YesY
ECHA InfoCard 100.002.863
EC Number 203-149-1
PubChem 7681
UNII TYP7AXQ1YJ YesY
Properties
C9H13N
Molar mass 135.21 g·mol−1
Appearance colourless to yellow 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[1] (27 °C)
Hazards
R-phrases R10, R20, R21, R22, R34, R52, R53
S-phrases S26, S36, S45, S61
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
3
0
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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Infobox references

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

Like some other benzyl compounds, the molecule undergoes directed ortho metalation with butyl lithium. Because of this reaction, many derivatives are known with the formula 2-X-C6H4CH2N(CH3)2 (X = SR, PR2, etc.).

The amine is basic and undergoes quaternization with methyl iodide to give the ammonium salt [C6H5CH2N(CH3)3]+I−.[2] Such salts are useful phase transfer catalysts.

N,N-Dimethylbenzylamine can be synthesized by methylation of benzylamine with formic acid and formaldehyde according to the Eschweiler–Clarke reaction.[3][4][5]

References

  1. ↑ "Melting point".
  2. ↑ Brasen, W. R.; Hauser, C. R. (1963). "2-Methylbenzyldimethylamine". Org. Synth.; Coll. Vol., 4, p. 585
  3. ↑ Eschweiler, W. (1905). "Ersatz von an Stickstoff gebundenen Wasserstoffatomen durch die Methylgruppe mit Hülfe von Formaldehyd". Chem. Ber. 38: 880. doi:10.1002/cber.190503801154.
  4. ↑ 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.
  5. ↑ Icke, R. N.; Wisegarver, B. B.; Alles, G. A. (1945). "β-Phenylethyldimethylamine". Org. Synth.; Coll. Vol., 3, p. 723
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