1.3- Dichloro-4,6-dinitrobenzene

Dinitro-l, 3-bis( f -hy droxyetby lamino)-benzene orn-yel ndls (from ale), having a bitter taste, mp 211° practically insol in eth, petr eth, chlf, benz Sc toluene si sol in w, was prepd by treating an alcoholic soln of 1,3-dichloro-4,6-dinitrobenzene with 4 equivs of jS-hydroxyethylamine (Ref 3). 

See 1,5-Dichloro-2,4-dinitrobenzene Dimethyl sulfoxide, etc. See other haloaryl compounds, polynitroaryl compounds... 

Table 3 presents the experimental enthalpies of formation of polynitrobenzenes and Table 4 presents the calculated additivity values and DSEs for these same compounds. Enthalpy-of-formation values have been determined experimentally for all three dinitrobenzene isomers in the gaseous state. The enthalpy-of-formation difference between the meta and para isomers is indistinguishable from 0. Conventional wisdom suggests that the para isomer should be destabilized relative to the meta because of adjacent positive charges in key ionic or polar resonance structures. Thus it seems that electronic effects due to meta/para dinitro substituent position are small. This small enthalpy-of-formation difference is similar to that for the meta and para dicyano, difluoro and dichloro benzenes, but does not mimic the ca 22 kJ mol 1 difference for the phthalic acids with which the... 

Dichloro-2,4-dinitrobenzene, 2077 2,4,-Dichloronitrobenzene, 2104 3,4-Dichloronitrobenzene, 2105 Dichlorophenol mixed isomers, 2161 f 1,3-Difluorobenzene, 2168 f 1,4-Difluorobenzene, 2169... 

A,A -Bis(3-aminopicryl)-l,2-ethanediamine (108) (m.p. 275 °C) is prepared from the reaction of ethylenediamine with two equivalents of 3-chloro-2,4,6-trinitroaniline. " The same chemists reported 3,3 -diamino-2,2 4,4, 6,6 -hexanitrodiphenylamine (109), a heat resistant explosive (m.p. 232-237 °C) prepared from the reaction of l,3-dichloro-4,6-dinitrobenzene with 3-chloroaniline followed by mixed acid nitration and subsequent chloro group displacement with ammonia. The potassium salt of 3,3 -diamino-2,2, 4,4, 6,6 -hexanitrodiphenylamine shows very high thermal stability. " ... 

Similar routes have been used for the synthesis of other polynitrophenylenes. 1,3,5-Tris(2,4,6-trinitrophenyl)-2,4,6-trinitrobenzene (160) is synthesized from the reaction of 1,3,5-trichloro-2,4,6-trinitrobenzene with three equivalents of picryl chloride in the presence of activated copper powder in refluxing mesitylene. " 2,2",4,4, 4",6,6, 6"-Octanitro-m-terphenyl (161) has been synthesized from picryl chloride and l,3-dichloro-4,6-dinitrobenzene. ... 

Pagoria and co-workers synthesized a number of thermally stable explosives from the reaction of the sodium salt of ANTA with chloro-substituted arylenes and A-heterocycles. These include the synthesis of (117) from picryl ehloride, PRAN (118) from 2-chloro-3,5-dinitropyridine, IHNX (119) from 2,4-dichloro-5-nitropyrimidine, (120) from 1,5-dichloro-2,4-dinitrobenzene, and (121) from 4-chloro-6-(3-nitro-l,2,4-triazolyl)-5-nitropyrimidine. Coburn and co-workers " reported the synthesis of the tetrazine (122) and the triazine (123) from the reaction of the sodium salt of ANTA with 3,6-dichlorotetrazine and cyanuric chloride respectively. 

The nitration of l,3,5-trichloro-2-nitrobenzene (8) to l,3,5-trichloro-2,4-dinitrobenzene (9) with dinitrogen pentoxide in absolute nitric acid goes to completion in only 2-4 minutes at 32-35 °C. Further nitration of (9) would yield l,3,5-trichloro-2,4,6-trinitrobenzene (10) which undergoes ammonolysis on treatment with ammonia in toluene to give the thermally stable explosive 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) (11). The same sequence of reactions with l,3-dichloro-2-nitrobenzene provides a route to l,3-diamino-2,4,6-trinitrobenzene (DATE). Such reactions are clean and occur in essentially quantitative yield. 

Chloro-2,4-dinitrobenzene, 2091 4-Chloro-2,5 -diethoxynitrobenzene, 3295 4-Chloro-2-methylphenol, 2737 2-Chloro-5-nitrobenzenesulfonic acid, 2137 Chlorobenzene, 2221 f 2-Chlorofluorobenzene, 2127 f 3-Chlorofluorobenzene, 2128 f 4-Chlorofluorobenzene, 2129 2-Chloronitrobenzene, 2134 4-Chloronitrobenzene, 2135 4-Chlorotrifluoromethylbenzene, 2642 1,5-Dichloro-2,4-dinitrobenzene, 2070... 

Holleman [38] obtained very pure 1,4-dichloro-2,6-dinitrobenzene in the following way ... 

The reactivity of the nitro groups in l,4-dichloro-2,3-dinitrobenzene and 1,4-dichloro-2,5-dinitrobenzene is exceptionally high, exceeding that of the chlorine atom. 

Dinitro-4,3-dichlorobenzene, listed in Ref 16 as l,2-Dichloro-3,5-dinitrobenzene, grn-yel crysts (from ale), mp 56° was obtd together with l,2-dinitro-3,4-dichlorobenzene by nitrating l-nitro-2,3-dichlorobenzene with mixed acids (Ref 6) an expl 77% as powerful as PA 85% as powerful as TNT (by Trauzl test) and less sensitive to impact than TNT or PA (120% PA by Brit FI test)... 

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