N -methylideneaniline

Structural formula
General
Surname	N -methylideneaniline
other names	N -methylideneaniline; N -methylideneaminobenzene;
Molecular formula	C 7 H 7 N
External identifiers / databases
EC number	202-871-4
ECHA InfoCard	100.002.611
PubChem	66014
Wikidata	Q1959600
properties
Molar mass	105.14 g mol −1
Physical state	firmly
Melting point	142-144 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -Methylideneaniline or N -Methylidenaminobenzene is an organic chemical compound and is one of the simplest azomethines . Like dibenzalacetone and benzalaniline , it is used in organometallic chemistry , for example as a ligand to palladium , titanium and platinum and as an intermediate in the synthesis of N -methylaniline .

Reactivity

Due to the double bond and the reactive methylidene group, the molecule has a high reactivity (like benzalaniline ) and can react with many other compounds . The polarized C = N double bond is therefore a good point of attack for nucleophilic and electrophilic particles. Nucleophiles attack the carbon atom of the C = N double bond, while electrophiles attack the nitrogen atom . The substance can easily be hydrogenated to N -methylaniline on the zeolite Y catalyst .

properties

N -methylideneaniline is an odorless, orange-red powder consisting of mixed crystals. The substance is insoluble in water, partially dissolves in chloroform and very well in concentrated sulfuric acid .

presentation

N -methylideneaniline is formed by condensation of aniline and formaldehyde in the presence of water-releasing agents or on a zeolite Y catalyst. Formally, one equivalent of formaldehyde reacts with one equivalent of aniline to form N -methylideneaniline.

In the first step engages nitrogen atom whose free electron pair , the carbonyl group ( aldehyde group ) of the formaldehyde. The double bonded oxygen atom of the carbonyl group becomes a negatively charged, single bonded oxygen atom. In the next step, the nitrogen releases its proton to the negatively charged oxygen atom - a hydroxyl group is formed . With subsequent elimination of water , the N- methylideneaniline is then formed .

Reaction mechanism for the formation of N -methylideneaniline

Individual evidence

↑ JM Patterson, C.-Y. Shiue, WT Smith Jr .: Benzonitrile formation in the pyrolysis of aromatic nitrogen compounds , in J. Org. Chem. 1973 , 38 , 2447-2450; doi : 10.1021 / jo00954a007 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ ^A ^b ^c E. V. Steen (ed.), C. Claeys (ed.): Recent advances in the science and technology of zeolites and related materials: proceedings of the 14th International Zeolite Conference, Cape Town, South Africa, 25-30. April 2004, Part 3, Gulf Professional Publishing, 2004, ISBN 978-0-444-51825-5 , pp. 2221-2227.

[1] JM Patterson, C.-Y. Shiue, WT Smith Jr .: Benzonitrile formation in the pyrolysis of aromatic nitrogen compounds , in J. Org. Chem. 1973 , 38 , 2447-2450; doi : 10.1021 / jo00954a007 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[steen-3] A ^b ^c E. V. Steen (ed.), C. Claeys (ed.): Recent advances in the science and technology of zeolites and related materials: proceedings of the 14th International Zeolite Conference, Cape Town, South Africa, 25-30. April 2004, Part 3, Gulf Professional Publishing, 2004, ISBN 978-0-444-51825-5 , pp. 2221-2227.