Benzalaniline

Structural formula
General
Surname	Benzalaniline
other names	Benzalaniline Benzylidene aniline N - (phenylmethylidene) aniline
Molecular formula	C 13 H 11 N
Brief description	yellow solid
External identifiers / databases
CAS number 538-51-2 EC number 208-694-9 ECHA InfoCard 100.007.906 PubChem 10858 ChemSpider 10294712 Wikidata Q818455
properties
Molar mass	181.23 g mol −1
Physical state	firmly
density	1.038 g cm −3 (55  ° C )
Melting point	54 ° C
boiling point	310 ° C
solubility	almost insoluble in water, easily soluble in ethanol and diethyl ether
Refractive index	1,600 (100 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 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

Benzalaniline or more correctly benzylideneaniline is an organic chemical compound and belongs to the azomethines .

Because of the polar N = CH double bond , this molecule is a good point of attack for nucleophilic reaction partners.

properties

Benzylidene aniline in its pure form ( reaction of freshly distilled aniline with benzaldehyde ) is a yellow powder with a marzipan-like odor. If, however, brown aniline is used in the representation , the color of the benzalaniline tends to change into yellow-green or yellow-gray. The substance is insoluble in water, but dissolves very well in organic solvents such as ethanol , diethyl ether , dichloromethane (DCM) and chloroform .

Extraction and presentation

Benzalaniline is formed by a condensation reaction of aniline with benzaldehyde ( carbonyl component ) with elimination of water. One equivalent of benzaldehyde reacts with one equivalent of aniline to form benzylidene aniline. The reaction equation follows:

${\displaystyle \mathrm {C_{6}H_{5}NH_{2}+C_{6}H_{5}CHO\longrightarrow C_{6}H_{5}N{=}CHC_{6}H_{5}+H_{2}O} }$

use

Like dibenzalacetone , benzalaniline is also used in organometallic chemistry , for example as a ligand in complexes of palladium , titanium or molybdenum .

Individual evidence

1. ↑ Benzalaniline data sheet from AlfaAesar, accessed on December 15, 2010 ( PDF )(JavaScript required) .
2. ↑ ^{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. 3-430.
3. ↑ ^{a b} Claudia Synowietz (Ed.): Pocket book for chemists and physicists . founded by Jean d'Ans, Ellen Lax. 4th edition. Volume II: Organic Compounds . Springer, Berlin 1983, ISBN 3-540-12263-X .
4. ↑ Entry on benzalaniline in the ChemIDplus database of the United States National Library of Medicine (NLM)
5. ↑ ^{a b} Benzalaniline data sheet from Sigma-Aldrich , accessed on March 10, 2011 ( PDF ).
6. ↑ A. Meller, W. Maringgele, K. Hennemuth: Implementation of metal and metalloid compounds with multifunctional molecules. XXIII. Synthesis of asymmetric mono-, bis- and trisaminoboranes , in: Journal for inorganic and general chemistry , 1979 , 449 , pp. 77-82; doi : 10.1002 / zaac.19794490107 .
7. ↑ European patent application
8. ↑ J. Okuda, GE Herberich, E. Raabe, I. Bernal: The crystal and molecular structure of (η ² -benzylideneaniline) to (η ⁵ -cyclopentadienyl) molybdenum, a molybdenocene complex with side-on bound imine , in : J. Organomet. Chem. , 1988 , 353 , pp. 65-71; doi : 10.1016 / 0022-328X (88) 80300-0 .