N -allylaniline

Structural formula
General
Surname	N -allylaniline
other names	N - (2-propenyl) aniline; 3- ( N -phenylamino) propene; N -Allyl- N -phenylamine; N -2-propenylaniline; N- phenylallylamine; N -allylbenzene amine;
Molecular formula	C 9 H 11 N
Brief description	colorless liquid
External identifiers / databases
EC number	209-633-9
ECHA InfoCard	100,008,759
PubChem	68525
ChemSpider	61800
DrugBank	DB02870
Wikidata	Q165003
properties
Molar mass	133.19 g mol −1
Physical state	liquid
density	0.98 g cm −3 (20 ° C)
boiling point	219 ° C
Refractive index	1.563 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-315-319-332-335
	P: 261-280-305 + 351 + 338
	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 .

[sigma-1] Data sheet N-Allylaniline from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).

[2] Data sheet N-allylaniline from Acros, accessed on July 17, 2010.

[CRC90_3_12-3] 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.

[4] 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 .

[5] FL Carnahan, CD Hurd: Pyrolysis pf Allylanilines , in: J. Am. Chem. Soc 1930 , 52 , 4586-4595; doi : 10.1021 / ja01374a062 .

[6] 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 .

[7] 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 .

[8] Wilhelm Koenigs : Synthesis of the quinoline from allylaniline , in: Chem. Ber. 1879 , 12 , 453; doi : 10.1002 / cber.187901201128 .