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Dimethylbenzylamine

Chemical compound From Wikipedia, the free encyclopedia

Dimethylbenzylamine

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.

Quick Facts Names, Identifiers ...
Dimethylbenzylamine
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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
EC Number
  • 203-149-1
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 Y
    Key: XXBDWLFCJWSEKW-UHFFFAOYSA-N Y
  • 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
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
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
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)
ThumbHealth 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).
N verify (what is YN ?)
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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

External links

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