3995-39-9

Upstream product

• 75-03-6 ethyl iodide 
• 108-69-0 3,5-dimethylaminoaniline 
• 461-97-2 3,5-dimethylfluorobenzene 
• 109-89-7 diethylamine 
• 773-01-3 2,4,6-trimethylpyrylium tetrafluoroborate 
• 74-96-4 ethyl bromide 
• 874-63-5 3,5-dimethylmethoxybenzene 

Downstream Products

• 67793-03-7 3,5-dimethyl-4-nitroso-N,N-diethylaniline 
• 723733-82-2 (3,5-Dimethyl-4-nitro-phenyl)-diethyl-amine 
• 1380544-22-8 4,4'-methylenebis(N,N-diethyl-3,5-dimethylaniline) 
• 24672-76-2 9,10-bis-(4-methoxy-phenyl)-anthracene 
• 129371-69-3 4-(4-diethylamino-2,6-dimethylphenylimino)-1,4-dihydronaphthylidenemalononitrile 
• 2359-40-2 2,6-dimethyl-4-(diethylamino)aniline 

Relevant academic research and scientific papers

Cu(ii)-catalyzed C-H (SP3) oxidation and C-N cleavage: Base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source

Base-switched methylenation and formylation using tetramethylethylenediamine (TMEDA) as a carbon source have been achieved under mild conditions, catalyzed by CuCl2, with atmospheric oxygen as oxidant. Bisindolylmethanes, diphenylmethanes and 3-formylindoles were synthesized with excellent regioselectivity and good yield.

Naphthalene-1,8-diylbis(diphenylmethylium) as an organic two-electron oxidant: Benzidine synthesis via oxidative self-coupling of N,N-dialkylanilines

Naphthalene-1,8-diylbis(diphenylmethylium) exhibits a unique electron-transfer reduction behavior due to the close proximity of the two triarylmethyl cations, which form a C-C bond while accepting two electrons, leading to 1,1,2,2-tetraphenylacenaphthene. The preparation of the dication was readily accomplished under anhydrous conditions starting from a cyclic bis(triarylmethyl) ether, derived from 1,8-dibromonaphthalene. The process proceeded via deoxygenation accompanying the formation of a disiloxane on treatment with a silylating agent (Me3SiClO4 or Me 3SiOTf) in 1,1,1,3,3,3-hexafluoropropan-2-ol. The dication was successfully employed for oxidative coupling of N,N-dialkylanilines at the paraposition to afford the corresponding benzidines in good to excellent yield.

1,8-Bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: Synthesis of benzidines via self-coupling of N,N-Dialkylanilines

(Chemical equation presented) 1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions.

Experimental and theoretical study of near-infrared absorbing naphthoquinone methide dyes with a nonplanar geometry

The bathochromic shift of the near-infrared absorption spectra of naphthoquinone methide dyes has been observed as a function of increased steric hindrance between the quinone imine and aniline segments. This novel shift that results from the loss of plan

SYNTHESE DE N,N-DIALKYL-3,5-DIALKYL-ANILINES A PARTIR DES SELS DE TRIALKYL-2,4,6-PYRYLIUM

We have optimized through an experimental design the synthesis of N,N-diethyl-3,5-dimethylaniline from 2,4,6-trimethylpyrylium terafluoroborate (I) and diethylamine in a new reaction medium (acetonitrile/triethylamine).Optimal conditions have been applied with high yields to the synthesis of various 3,5-dimethylanilines derived from I and dimethylamine, morpholine, N-methylpiperazine, piperazine, dihexylamine, piperidine, and pyrrolidine respectively. 2-Alkyl-4,6-dimethylpyrylium tetrafluoroborates react regioselectively with diethylamine to afford N,N-diethyl-3-alkyl-5-methyl anilines under these conditions.

A Mechanism for the Photosubstitution of Fluoro- and Methoxy-benzenes by Diethylamine

The photochemical reactions of fluoro- and methoxy-benzenes with diethylamine produce addition and substitution products.The proposed mechanism involves quenching of the singlet state by the amine to give an exciplex.Proton transfer within the exciplex leads to the amine adducts, some of which can undergo elimination to yield the substitution products.