610-31-1Relevant articles and documents
Nitration of some di- and tri-nitrohalobenzenes with solid sodium nitrite in the presence of 18 crown 6
Badea, Florin,Stoica, Alice,Ioni?ǎ, Petre,Cǎproiu, Miron T.,Constantinescu, Titus
, p. 351 - 356 (2007/10/03)
1-Halo-4-R1-6-R2-2-nitrobenzenes 1a-d (where a : hal = F, R1 = NO2, R2=H; b: hal = Cl, R1 = NO2, R2 = H; c: hal = Cl, R1 = H, R2 = NO2 ; d: hal = Cl, R1 = CF3, R2 = NO2; ) and 1-chloro-2,4,6-trinitrobezene 1e were nitrated in methylene chloride with solid sodium nitrite in the presence of 18C6, and afforded the corresponding nitroderivatives 4-R1-6-R2-1,2-dinitrobenzenes 3a-c (where a: R1 = NO2, R2 = H; b: R1 = H, R2 = NO2; c: R1 = CF3, R2 = NO2; ) and 1,2,3,5-tetranitrobenzene 3d, respectively. The yields of this nucleophilic process depended on the number of nitro substituents and on the halogene type. UV-VIS and NMR spectra, TLC behaviour and pH-depending repartition in biphasic system water/methylene chloride of the synthecized compounds 3a-d are presented.
The Reaction of Nitrobenzenes with Sodium Borohydride; a Novel Reductive Coupling to Diphenylamine Derivatives
Dale, Johannes,Vikersveen, Line
, p. 354 - 361 (2007/10/02)
The reduction of mono-, di-, and trinitro-substituted benzenes by NaBH4 in hydroxylic solvents gives very different products depending on structure and reaction conditions.In addition to known reactions, such as formation of azoxybenzene and azobenzene derivatives, displacement of nitro groups by hydrogen, and ring reduction, a novel coupling reaction with loss of one nitro group was observed.From 1,3-dinitrobenzene and 1,3,5-trinitrobenzene, diphenylamine derivatives were obtained in reactions that are clean and of preparative value when the nitro compound is present in exess.From 1,2-dinitrobenzene the diphenylhydroxylamine derivative was obtained in a much slower, but equally clean reaction.Possible mechanisms are discussed, and an aromatic ipso radical substitution of a nitro group by a phenylnitroxide intermediate is proposed.
1,2,4-TRINITROBENZENE AS A THIOL REAGENT
Takahashi, Seitaro,Kokubo, Masayuki,Satake, Kazuo
, p. 1445 - 1448 (2007/10/02)
The 2,4-dinitrophenylation of thiol or amino group with 1,2,4-trinitrobenzene proceeded quantitatively at pH 8.5 and 30 deg C.The rate of S-dinitrophenylation was ca. 1E4 times faster than that of N-dinitrophenylation.So this reaction can be used for both the determination of thiol even in the presence of large excess amine and the specific modification of thiol in proteins.