Electrophilic fluorination of N,N-dimethylaniline, N,N-dimethylnaphthalen-1-amine and 1,8-bis(dimethylamino)naphthalene with N-F reagents was written by Sorokin, Vladimir I.;Pozharskii, Alexander F.;Ozeryanskii, Valery A.. And the article was included in Journal of Fluorine Chemistry in 2013.Safety of 2-Chloro-N,N-dimethylaniline This article mentions the following:
Reaction of N,N-dimethylaniline, N,N-dimethylnaphthalen-1-amine and 1,8-bis(dimethylamino)naphthalene (proton sponge) with 1-chloromethyl-4-fluorodiazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) and N-fluorobenzenesulfonimide (NFSI) has been studied under various conditions. Unlike the proton sponge, which is fluorinated rather selectively at the ortho-position to NMe2 group, producing 2-fluoro derivatives in moderate yield, two other amines react with Selectfluor and NFSI with strong tarring and the formation of complex mixtures of the corresponding biaryls, biarylmethanes and N-demethylated products. 2-Fluoro and 4-fluoro derivatives are also formed in minor quantities with the former isomer being predominant. Using the NFSI-ZrCl4 system results in competitive chlorination of the aromatic ring. In the experiment, the researchers used many compounds, for example, 2-Chloro-N,N-dimethylaniline (cas: 698-01-1Safety of 2-Chloro-N,N-dimethylaniline).
2-Chloro-N,N-dimethylaniline (cas: 698-01-1) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Safety of 2-Chloro-N,N-dimethylaniline
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics