121904-46-9Relevant articles and documents
Polyhalogenonitrobenzenes and Derived Compounds. Part 3. Reactions of 1,2,3,4-Tetrachloro-5,6-dinitrobenzene with Bidentate Nucleophiles
Heaton, Alan,Hill, Mark G.,Hunt, Michael H.,Drakesmith, Frederick G.
, p. 401 - 404 (2007/10/02)
1,2,3,4-Tetrachloro-5,6-dinitrobenzene (TCDNB) has been treated with a number of bidentate nucleophiles, all of which contained at least one amino or methylamino group.Diamines of the type H2N(CH2)nNHR (R=H or Me, n=2,3, or 5), reacted via the primary amino group displacing a nitro group from TCDNB.The resulting products were inert to further reaction, i.e.Cyclisation or further nucleophilic substitution.Both 2-hydroxyethylamine and ethyl glycinate behaved similarly, although ethyl diazoacetate was a by-product in the latter reaction.The reaction of TCDNB with hydrazine hydrate was very sensitive to the conditions employed, i.e. rapid addition of excess of reagent (2.2:1 molar ratio) gave 3,4,5,6-tetrachloro-o-phenylenediamine (reduction had occured).Slow addition of an equimolar amount yielded 2,3,4,5-tetrachloro-6-nitrophenylhydrazine, i.e. nucleophilic substitution.N,N'-Dimethylethylenediamine and 2-hydroxy-N-methylethylamine reacted with TCDNB to give cyclised products, i.e. both nucleophilic centres reacted.The course of these reactions was investigated.In contrast 2-acetoxyethylamine, glycine, urea, 2,2'-iminodiethanol and butane-1,1,4,4-tetra-amine were all unreactive towards TCDNB.
