Dibenzylaniline

Dibenzylaniline
Names
	Preferred IUPAC name N,N-Dibenzylaniline
Identifiers
CAS Number	91-73-6;
3D model (JSmol)	Interactive image;
ChemSpider	60047;
EC Number	202-093-5;
PubChem CID	66681;
UNII	6GF9B456WW ;
CompTox Dashboard (EPA)	DTXSID5059030;
	InChI InChI=1S/C20H19N/c1-4-10-18(11-5-1)16-21(20-14-8-3-9-15-20)17-19-12-6-2-7-13-19/h1-15H,16-17H2 Key: ISGXOWLMGOPVPB-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)CN(CC2=CC=CC=C2)C3=CC=CC=C3;
Properties
Chemical formula	C20H19N
Molar mass	273.379 g·mol−1
Appearance	yellowish white crystals
Melting point	69.0 °C (156.2 °F; 342.1 K)
Boiling point	300 °C (572 °F; 573 K) above
Solubility in water	insol
Solubility	ether, ethanol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319
Precautionary statements	P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dibenzylaniline or N,N-Dibenzylaniline is a chemical compound consisting of aniline with two benzyl groups as substituents on the nitrogen.

The substance crystallizes in the monoclinic crystal system. The space group is P2₁/n. The unit cell dimensions are a=11.751 Å b=9.060 Å c=29.522 Å, and β=94.589°.[1] Each unit cell contains two molecules. In the solid van der Waals forces hold it together.[2] The substance can also crystallize in alternate monoclinic form.[3]

Production

One method to produce dibenzylaniline is using a mixture of dibutyl tin dichloride and dibutyl stannane with N-benzilideneaniline along with hexamethylphosphoric triamide dissolved in tetrahydrofuran which yields a tin amide compound. This then reacts with benzyl bromide to yield dibenzylaniline.[4]

Another method uses aniline and benzyl bromide.

Use

It used to make dyes.

A nitroso derivative (made using nitrite and hydroxylamine) can be used in a colourimetric test for palladium.[5]

References

Bi, Quan-Xi; Tong, Hong-Bo; Zhou, Mei-Su (2007). "Crystal Structure". CCDC 642961: Experimental Crystal Structure Determination. Cambridge Crystallographic Data Centre. doi:10.5517/ccpl1pz.
Bi, Quan-Xi; Tong, Hong-Bo; Zhou, Mei-Su (21 March 2007). "N,N-Dibenzylaniline". Acta Crystallographica Section E. 63 (4): o1809–o1810. doi:10.1107/S1600536807011476.
Tong, Hong-Bo; Zhou, Mei-Su; Bi, Quan-Xi; Chao, Jian-Bin (7 November 2007). "A new polymorph of N,N-dibenzylaniline". Acta Crystallographica Section E. 63 (12): o4560. doi:10.1107/S1600536807054402.
Fürstner, Alois (2014). Science of Synthesis Knowledge Updates 2013. Georg Thieme Verlag. pp. 72–73. ISBN 978-3-13-178881-8.
Brooks, Robert R. (1992). Noble Metals and Biological Systems: Their Role in Medicine, Mineral Exploration, and the Environment. CRC Press. p. 142. ISBN 978-0-8493-6164-7.

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[1] Bi, Quan-Xi; Tong, Hong-Bo; Zhou, Mei-Su (2007). "Crystal Structure". CCDC 642961: Experimental Crystal Structure Determination. Cambridge Crystallographic Data Centre. doi:10.5517/ccpl1pz.

[2] Bi, Quan-Xi; Tong, Hong-Bo; Zhou, Mei-Su (21 March 2007). "N,N-Dibenzylaniline". Acta Crystallographica Section E. 63 (4): o1809–o1810. doi:10.1107/S1600536807011476.

[3] Tong, Hong-Bo; Zhou, Mei-Su; Bi, Quan-Xi; Chao, Jian-Bin (7 November 2007). "A new polymorph of N,N-dibenzylaniline". Acta Crystallographica Section E. 63 (12): o4560. doi:10.1107/S1600536807054402.

[4] Fürstner, Alois (2014). Science of Synthesis Knowledge Updates 2013. Georg Thieme Verlag. pp. 72–73. ISBN 978-3-13-178881-8.

[5] Brooks, Robert R. (1992). Noble Metals and Biological Systems: Their Role in Medicine, Mineral Exploration, and the Environment. CRC Press. p. 142. ISBN 978-0-8493-6164-7.