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Dibenzylaniline

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Dibenzylaniline
Names
Preferred IUPAC name N,N-Dibenzylaniline
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 202-093-5
PubChem CID
UNII
CompTox Dashboard (EPA)
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,16-17H2Key: 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
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 GHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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°. Each unit cell contains two molecules. In the solid van der Waals forces hold it together. The substance can also crystallize in alternate monoclinic form.

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.

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.

References

  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. Bibcode:2007AcCrE..63O1809B. 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. Bibcode:2007AcCrE..63O4560T. 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.


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