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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