N -allylaniline
Structural formula | ||||||||||||||||||||||
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General | ||||||||||||||||||||||
Surname | N -allylaniline | |||||||||||||||||||||
other names |
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Molecular formula | C 9 H 11 N | |||||||||||||||||||||
Brief description |
colorless liquid |
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properties | ||||||||||||||||||||||
Molar mass | 133.19 g mol −1 | |||||||||||||||||||||
Physical state |
liquid |
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density |
0.98 g cm −3 (20 ° C) |
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boiling point |
219 ° C |
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Refractive index |
1.563 (20 ° C) |
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safety instructions | ||||||||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
N -Allylaniline is an organic compound . It consists of an aniline framework that has an allyl group on the nitrogen atom.
presentation
N -Allylaniline can be produced by alkylating aniline with allyl chloride , bromide or iodide . The synthesis by Ullmann amination from allylamine and phenyl iodide is also known.
Historically, N -allylaniline led to the elucidation of the structure of quinoline , which could be synthesized from N -allylaniline in 1880 using lead oxide .
Individual evidence
- ↑ a b c Data sheet N-Allylaniline from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).
- ↑ Data sheet N-allylaniline from Acros, accessed on July 17, 2010.
- ↑ a b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-12.
- ↑ H. Oehme, R. Thamm: Synthesis and reaction behavior of (3-aminopropy1) -phenylphosphines , in: J. Prakt. Chem 1973 , 315 , 526-538; doi : 10.1002 / prac.19733150320 .
- ↑ FL Carnahan, CD Hurd: Pyrolysis pf Allylanilines , in: J. Am. Chem. Soc 1930 , 52 , 4586-4595; doi : 10.1021 / ja01374a062 .
- ^ V. Pace, F. Martinez, M. Fernandez, JV Sinisterra, AR Alcantara: Effective Monoallylation of Anilines Catalyzed by Supported KF , in: Org. Lett. 2007 , 9 , 2661-2664; doi : 10.1021 / ol070890o .
- ↑ D. Ma, Q. Cai, H. Zhang: Mild Method for Ullmann Coupling Reaction of Amines and Aryl Halides , in: Org. Lett. 2003 , 5 , 2453-2456; doi : 10.1021 / ol0346584 .
- ↑ Wilhelm Koenigs : Synthesis of the quinoline from allylaniline , in: Chem. Ber. 1879 , 12 , 453; doi : 10.1002 / cber.187901201128 .