Tribenzylamine

Tribenzylamine
Identifiers
CAS Number	620-40-6;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3184803;
ChemSpider	22739;
ECHA InfoCard	100.009.673
EC Number	210-638-3;
PubChem CID	24321;
UNII	HZ10O1931J;
CompTox Dashboard (EPA)	DTXSID5047031 ;
	InChI InChI=1S/C21H21N/c1-4-10-19(11-5-1)16-22(17-20-12-6-2-7-13-20)18-21-14-8-3-9-15-21/h1-15H,16-18H2 Key: MXHTZQSKTCCMFG-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)CN(CC2=CC=CC=C2)CC3=CC=CC=C3;
Properties
Chemical formula	C21H21N
Molar mass	287.406 g·mol−1
Appearance	white solid
Melting point	91.5 °C (196.7 °F; 364.6 K)
Boiling point	385 °C (725 °F; 658 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tribenzylamine is an organic compound with the formula N(CH₂C₆H₅)₃. It is a symmetrical tertiary amine. It is of some historic interest as one of the first compounds produced by the Leuckart reaction.^[1]

The compound is a common target in the development of new synthetic methods, e.g. from benzyl alcohol.^[2]^[3]

References

^ Leuckart, R. (1885). "Ueber eine neue Bildungsweise von Tribenzylamin". Berichte der Deutschen Chemischen Gesellschaft. 18 (2): 2341–2344. doi:10.1002/cber.188501802113.
^ Hamid, M. Haniti S. A.; Allen, C. Liana; Lamb, Gareth W.; Maxwell, Aoife C.; Maytum, Hannah C.; Watson, Andrew J. A.; Williams, Jonathan M. J. (2009). "Ruthenium-Catalyzed N -Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology". Journal of the American Chemical Society. 131 (5): 1766–1774. Bibcode:2009JAChS.131.1766H. doi:10.1021/ja807323a. PMID 19191700.
^ Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei (2010). "Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir−Ammine Complexes". Journal of the American Chemical Society. 132 (43): 15108–15111. Bibcode:2010JAChS.13215108K. doi:10.1021/ja107274w. PMID 20931960.

[1] Leuckart, R. (1885). "Ueber eine neue Bildungsweise von Tribenzylamin". Berichte der Deutschen Chemischen Gesellschaft. 18 (2): 2341–2344. doi:10.1002/cber.188501802113.

[2] Hamid, M. Haniti S. A.; Allen, C. Liana; Lamb, Gareth W.; Maxwell, Aoife C.; Maytum, Hannah C.; Watson, Andrew J. A.; Williams, Jonathan M. J. (2009). "Ruthenium-Catalyzed N -Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology". Journal of the American Chemical Society. 131 (5): 1766–1774. Bibcode:2009JAChS.131.1766H. doi:10.1021/ja807323a. PMID 19191700.

[3] Kawahara, Ryoko; Fujita, Ken-Ichi; Yamaguchi, Ryohei (2010). "Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir−Ammine Complexes". Journal of the American Chemical Society. 132 (43): 15108–15111. Bibcode:2010JAChS.13215108K. doi:10.1021/ja107274w. PMID 20931960.

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