Dimethylbenzylamine

Last updated
Dimethylbenzylamine
Benzyldimethylamine.svg
Dimethylbenzylamine 3D ball.png
Names
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]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.863 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-149-1
PubChem CID
RTECS number
  • DP4500000
UNII
UN number 2619
  • InChI=1S/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 Yes check.svgY
    Key: XXBDWLFCJWSEKW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3
    Key: XXBDWLFCJWSEKW-UHFFFAOYAQ
  • N(C)(Cc1ccccc1)C
Properties
C9H13N
Molar mass 135.210 g·mol−1
Appearancecolourless 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
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H226, H302, H312, H314, H332, H412
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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. ↑ "N,N-dimethyl benzyl amine". The Good Scents Company. Retrieved 1 November 2020.
  2. ↑ Icke, R. N.; Wisegarver, B. B.; Alles, G. A. (1945). "β-Phenylethyldimethylamine". Organic Syntheses. 25: 89. doi:10.15227/orgsyn.025.0089.
  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. ↑ W. R. Brasen; C. R. Hauser (1954). "o-Methylethylbenzyl Alcohol". Org. Synth. 34: 58. doi:10.15227/orgsyn.034.0058.
  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. ↑ 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. ↑ 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. ↑ 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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