Dimethylbenzylamine

Dimethylbenzylamine
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
Identifiers
CAS Number	103-83-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL45591 ;
ChemSpider	7398 ;
ECHA InfoCard	100.002.863
EC Number	203-149-1;
PubChem CID	7681;
RTECS number	DP4500000;
UNII	TYP7AXQ1YJ ;
UN number	2619
CompTox Dashboard (EPA)	DTXSID8021854 ;
	InChI InChI=1S/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 Key: XXBDWLFCJWSEKW-UHFFFAOYSA-N ; InChI=1/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 Key: XXBDWLFCJWSEKW-UHFFFAOYAQ;
	SMILES N(C)(Cc1ccccc1)C;
Properties
Chemical formula	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)
Solubility in water	1.2 g/100mL
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H312, H314, H332, H412
Precautionary statements	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)	3 3 0
Flash point	55 °C (131 °F; 328 K)
Autoignition; temperature	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). verify (what is ?) Infobox references

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.

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

^ "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.
^ W. R. Brasen; C. R. Hauser (1954). "o-Methylethylbenzyl Alcohol". Org. Synth. 34: 58. doi:10.15227/orgsyn.034.0058.
^ 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.
^ 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.
^ 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.
^ Mascorro, José A. (2003). "Benzyldimethylamine (BDMA): Catalyst of Choice with Epoxy Embedding Media". Microscopy Today. 11 (4): 47. doi:10.1017/s1551929500053104.

External links

Safety MSDS data Archived 2007-10-11 at the Wayback Machine

[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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