Tetranitroaniline

6-Tetranitroaniline (m. p. 215°C, decomposition) is a yellowish crystalline substance, difficult to dissolve in most of organic solvents but soluble in acetone (17 parts in the boiling solvent) and o- nitrotoluene (some 33 parts at 140°C). 

Tetranitroaniline was first obtained by Flurscheim [19, 19a], who proposed its use as an explosive because its properties were similar to those of tetryl. For the preparation of tetranitroaniline Flurscheim nitrated m- nitroaniline with a mixture of concentrated acids at 70-80°C. The yield was 64-69% of the theoretical (from 100 kg of m- nitroaniline only 130-140 kg instead of 204 kg could be obtained). 

Tetranitroaniline is a rather unstable compound. Thus, when boiled with water its meta- nitro group undergoes hydrolysis to a phenolic group (II), while on boiling with methyl- or ethyl alcohol it yields an anisole- (III) or phenetole derivative (IV), which with ammonia may form trinitro-m-phenylenediamine (V)  

Although, according to Fliirscheim, tetranitroaniline has sufficient thermal stability, even a product of the highest purity does not give a satisfactory heat test. 

According to Ingraham [19b], tetranitroaniline has shown evidence of decomposition by the heat test at 65.5°C when only a small amount of moisture was pie-sent. The main product of decompositions was II. Prolonged heating at 75°C results in loss of a nitro group. At 120°C decomposition takes place which proceeds in a way similar to that of tetryl. The initiation temperature is 231-233°C. The specific gravity of the product is 1.867 [19], 

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N-Methyl-N,2,4,6-tetranitroaniline Methyl vinyl ketone Metribuzin Mevinphos... 

Nitration to 2,3,4,6-tetranitroaniline proved unsafe in mixed acid at 30-50°C. Efficient and safe nitration at 20-30°C was obtained by dissolving the substrate in sulfuric acid, then adding mixed acid (made with oleum) thereto. 

Tellurium Tetrahydrofuran Tetranitroaniline Tetranitromethane Thiocyanates Thionyl chloride Thiophene Thymol Halogens, metals Tetrahydridoaluminates, KOH, NaOH Reducing materials Aluminum, cotton, aromatic nitro compounds, hydrocarbons, cotton, toluene Chlorates, nitric acid, peroxides Ammonia, dimethylsulfoxide, linseed oil, quinoline, sodium Nitric acid Acetanilide, antipyrine, camphor, chlorohydrate, menthol, quinine sulfate, ure- thene... 

Tetranitroanilin ist unloslich in Wasser, loslich in heiliem Eisessig und in heiliem Aceton, wenig loslich in Alkohol, Benzol, Ligroin und Chloroform. 

Tetranitroanilin kann durch Nitrieren von m-Nitroanilin Oder von Anilin mit einem Gemisch von Schwefelsaure und Salpetersaure in maRiger Ausbeute hergestellt werden. 

The tetranitroaniline is destabilized by steric interaction between three neighboring nitro groups. It has been used as an explosive booster (a moderately sensitive explosive between the detonator and the main charge that magnifies the shock from the detonator to start the detonation in the more insensitive main charge)94. 

Methyl n-propyl ketone, see 2-Pentanone a-Methylstyrol, see a-Methylstyrene Methyl sulfate, see Dimethyl sulfate Methyl sulfhydrate, see Methyl mercaptan IV-Methyl-IV,2,4,6-tetranitroaniline, see Tetryl IV-Methyl-IV,2,4,6-tetranitrobenzenamine, see Tetryl Methyl thioalcohol, see Methyl mercaptan Methyl thiram, see Thiram Methyl thiuramdisulfide, see Thiram /n-Methyltoluene, see m-Xylene o-Methyltoluene, see o-Xylene p-Methyltoluene, see p-Xylene Methyl tribromide, see Bromoform Methyl trichloride, see Chloroform Methyltrichloromethane, see 1,1,1-Trichloroethane... 

Nitration of m-nitroaniline (28) with fuming nitric acid and oleum yields 2,3,4,6-tetranitroaniline (29), a powerful but chemically unstable explosive. 2,3,4,6-Tetranitroaniline readily reacts with a range of nucleophiles, including water to yield 3-amino-2,4,6-trinitrophenol. 

Orlova and co-workers "i reacted 1,2,3,5-tetranitrobenzene with hydrochloric and hydro-bromic acids to form picryl chloride and picryl bromide respectively. The same chemists treated 2,3,4,6-tetranitroaniline and 2,3,4,6-tetranitrophenol (121) with aqueous solutions of hydrogen halides to form 3-halo-2,4,6-trinitroanilines and 3-halo-2,4,6-trinitrophenols (122 and 123) respectively. 

The nitration of both 4-methyl- and 4-chloro-2,6-dinitrotoluenes (66 and 67) with mixed acid in acetic acid at subambient temperature allows the isolation of the nitramines, (68) and (69), respectively. Thermolysis of (68) and (69) in refluxing methylene chloride yields the corresponding diazophenols, (70) and (71), respectively. Scilly and co-workers isolated 2-diazo-4,6-dinitrophenol (DINOL) (53) from the thermolysis of fV,2,3,5-tetranitroaniline (73) in ethyl acetate at 60 °C. 

Synonyms 2,4,6-Trinitrophenylmethyl-nitramine tetralite nitramine N-methyl-iV-2,4,6-tetranitroaniline... 

Aniline was also prepd and this gave on nitration the very powerful Tetranitroaniline which is described in Vol 1 of Encycl, pp A425ff. 

B. Fliirscheim patented the prepn of 2,3,4,6-Tetranitroaniline, one of the most powerful expls. It was used during WWI by the Germans and Japanese (Vol 1 of Encycl, pp A411 to A413)... 

This mixt is more powerful than TNT or Tetranitroaniline, but is insensitive to shock or friction and burns without detonation when dropped in a red hot crucible or ignited by flame. Its ignition temp is 194-208°. It cannot be stored for longer than 24-48 hours, as bubbles, resulting from decomposition of the H2 02, are evolved and the mass hardens. Moreover its explosive power decreased after 48 hours of standing (Ref 1)... 

N-Ethyl-N,2,4,6-tetranitroaniline (2,4,Trinit rapheny Ini tram ino)ethane N-Ethyl-N-nitro-2,4,6-trinitrooniline Ethylpicrylnitramine called by Blatt 2,4,6-Trinitrophenylethylnitromine and... 

N-Ethyl N,2,4,6-Tetranitroaniline or Ethyl Tetryl. See this Vol, p E207-L. The following information was not included there ... 

N)3C6H(NH.C2H5)2 mw 299.24, N 23.41% yel crysts mp 142-44° was prepd by heating N-nitro-N-ethyl-2,3,4,6-tetranitroaniline with ethylamine in a tube at 50-60°, or from 3-chloro-2,4,6-trinitrophenol ethylamine in ale. Its expl props were not reported Refs 1) Beil 13, 61 8t (17) 2) J.J. 

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