Baciocchi, Enrico et al. published their research in Journal of Organic Chemistry in 2010 | CAS: 4714-63-0

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. COA of Formula: C9H10N2

N-Demethylation of N,N-Dimethylanilines by the Benzotriazole N-Oxyl Radical: Evidence for a Two-Step Electron Transfer-Proton Transfer Mechanism was written by Baciocchi, Enrico;Bietti, Massimo;Lanzalunga, Osvaldo;Lapi, Andrea;Raponi, Daniele. And the article was included in Journal of Organic Chemistry in 2010.COA of Formula: C9H10N2 This article mentions the following:

The reaction of the benzotriazole N-oxyl radical (BTNO) with a series of 4-X-N,N-dimethylanilines (X = CN, CF3, CO2CH2CH3, CH3, OC6H5, OCH3) has been investigated in CH3CN. Product anal. shows that the radical, 4-X-C6H4N(CH3)CH2·, is first formed, which can lead to the N-demethylated product or the product of coupling with BTNO. Reaction rates were found to increase significantly by increasing the electron-donating power of the aryl substituents (ρ+ = -3.8). With electron-donating substituents (X = CH3, OC6H5, OCH3), no intermol. deuterium kinetic isotope effect (DKIE) and a substantial intramol. DKIE are observed With electron-withdrawing substituents (X = CN, CF3, CO2CH2CH3), substantial values of both intermol. and intramol. DKIEs are observed These results can be interpreted on the basis of an electron-transfer mechanism from the N,N-dimethylanilines to the BTNO radical followed by deprotonation of the anilinium radical cation (ET-PT mechanism). By applying the Marcus equation to the kinetic data for X = CH3, OC6H5, OCH3 (rate-determining ET), a reorganization energy for the ET reaction was determined (λBTNO/DMA = 32.1 kcal mol-1). From the self-exchange reorganization energy for the BTNO/BTNO– couple, a self-exchange reorganization energy value of 31.9 kcal mol-1 was calculated for the DMA·1/DMA couple. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0COA of Formula: C9H10N2).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. COA of Formula: C9H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts