1- Chloro-2,4,6-trinitrobenzene

A crystalline addition product of indole with picryl chloride (i.e. l-chloro-2,4,6-trinitrobenzene), together with an unidentified amorphous substance, were obtained by the action of picryl chloride on indole magnesium iodide, and analogous products were obtained in the reaction between the indole Grignard reagent and 1-chloro-2,4,5-trinitrobenzene. 

I-Chloro-2,4,6,-trinitrobenzene (picryl chloride) Trinitrobenzoic acid... 

These treatments have been also applied to S/yAr. For example, for a neutral nucleophile, all the classical pathways identified at present are represented by the general reaction mechanism shown by Scheme 2. A concerted mechanism, indicated by the diagonal path in Scheme 2, had not been discussed until lately, but was observed, among other systems, in the hydrolysis of l-chloro-2,4,6-trinitrobenzene and 1-picrylimidazole. The study was then extended to other related substrates and structure-reactivity relationships could be obtained78. 

Taking into account, for instance, the slight differences in K observed for l-fluoro-2,4,6-trinitrobenzene and 1 -chloro-2,4,6-trinitrobenzene in Table 13, it is difficult to explain such a difference in K /K. Nevertheless, a H/D isotopic effect of 1.5 could be easily explained... 

The thermally insensitive explosive (112) is synthesized by a similar route from the reaction of l,3-dichloro-2,4,6-trinitrobenzene (106) (styphnyl chloride) with two equivalents of 3-chloroaniline, followed by nitration and subsequent displacement of the chloro groups with... 

Laval and Vignane reported the synthesis of the nitrotriazole (124) from the reaction of 3-nitro-1,2,4-triazole with 3,5-diamino-l-chloro-2,4,6-trinitrobenzene. The nitrotriazole (124) is a useful secondary high explosive, exhibiting high performance and a low sensitivity to impact. 

Picryl chloride Plastic explosive l-Chloro-2,4,6-trinitrobenzene... 

Carboxy-l,3-diamino-2,4,6-trinitrobenzene 5-Nitro-2(3,5-diamino-2,4,6-trinitrophenol)-1,2,4-triazole 5-Nitroterazolecopper salt 5-Ureido-l,3-diamino-2,4,6-trinitrobenzene 7-Amino-4,6-dinitrobenzofuroxan 10-Chloro-5,10-dihydrophenarsazine Acetyltrinitro-cyclotetramethylene tetramine Acquinite... 

Following methods of prepn of HNDPhS are described in the literature a) Treating 2 mols of Chloro-2,4,6-trinitrobenzene (Picrylchloride) with.l mol of Na thiosulfate in water, followed by neutraliza-... 

Trinitroanilinoyindazole, called in Ref 2 1 Trinitrophenyl-B-l-Aminoindazol, (03 N)sC6Ha. NH.C7Hs Nj, mw 344.24, N 24.42%. Orange ndls(from benz+alc), mp 240—50°(decomp). Diff sol in most org solvents. Was prepd by treating 6-aminoindazole with 2-chloro-1,3,5 trinitrobenzene in ale soln and in the presence of Na acetate. Its expl props were not examined Refs l)Beil 25,317 2)E.Noelting,Ber 37, 2582(1904)... 

Trinitro-3 cbloroaniline or Methyl-(3 -chloro-2,4,6-trinitro-phenyl-ether), C1.C6H(N02)3.0.CH3 col crysts(from ale), mp 86-88° can be prepd by nitrating 3-chloronitro-anisole with nitric-sulfuric acid or by other methods. Its expl props were not detd Refs l)Beil 6, 292 [283] 2)J.J.Blanksma, Rec 21, 323(1902) [Called Oxymethylchloro-trinitrobenzene(1.3.2.4.6.)] 3)H.H.Schlubach F. Mergenthaler, Ber 58, 2734(1925 ) CA 20, 1395(1926)... 

A further example is provided by the reaction of l-chloro-2,4,6-trinitrobenzene (picryl chloride) with jV,jV-diphenylhydrazine to give N,N-diphenylpicrylhydrazine (Expt 6.94). This compound is of interest in that... 

Dissolve 7.4 g (0.04 mol) of AT,AT-diphenylhydrazine (Expt 6.95) in 10 ml of dry dichloromethane and add a solution of 5g (0.02 mol) of picryl chloride [1-chloro-2,4,6-trinitrobenzene, (1)] in 40 ml of dry dichloromethane. Shake the mixture, which becomes dark and warm, and set it aside for 1 hour. Cool the suspension in an ice bath, filter off the amine salt and wash it with a little dichloromethane. Concentrate the filtrate and washings to 30 ml (rotary evaporator) and treat the hot concentrate with 60 ml of boiling ethanol. Cool, collect the almost pure diphenylpicrylhydrazine which crystallises and wash it with a little cold ethanol. The yield is 6 g (76%), m.p. 172-173 °C (decomp.). If desired, the product may be recrystallised from ethyl acetate. 

For characterisation, aromatic hydrocarbons can be sulphonated, chloro-sulphonated, carboxybenzoylated and nitrated. Polynuclear aromatic hydrocarbons, and many of their derivatives, yield crystalline adducts with picric acid, styphnic acid, 1,3,5-trinitrobenzene and 2,4,7-trinitrofluorenone. 

---