Trinitro-anisole

NilTobenzamido) 2,3,5-trinitro-anisole, ndls(from MNB), mp 247° sol in hot AcOH, ale or acet insol in benz or Iigroin. Can be prepd by heating p-aniside of 3-nitrobenzoic acid with nitric acid(d 1.52) or by other methods. Its expl props were not detd (Refs 1 2) 4 (4 -Nitrobenzamido)-2,3,5 trinitro-aniso e, ndls(from 40% AcOH), mp 253° sol in acet sol in HNOs(d 1.4) diffc sol in ale. Can be prepd by heating the p-aniside of 4-nitrobenzoic acid with nitric acid(d 1.52). Its expl props were not detd... 

Smallest Amount (Grams) Which Will Cause Detonation oe Tetryl Picric Acid Trinitro- toluene Trinitro- anisol Trinitro- xylene... 

Table 2 (Ref 23) gives the condensed phase products of the thermal decompn of Tetryl at 160°. Aside from undecompd Tetryl, Trinitro-anisole is the major product, although it tends to disappear on prolonged heating apparently forming Picric Acid, whose concn rises sharply at long decompn times. Note that the amount of condensed phase decreases on long heating. Consequently long heating favors production of gaseous decompn products...

Tetryl 2,4,6-trinitro- anisole Picric Acid N-methyl-2,4,6- trinitroaniline... 

Fig. 1. NMR spectra (00 MHz), showing ring-proton resonances, of 2,4,6-trinitro-anisole plus O 6 equivalents of sodium methoxide in dimethyl sulphoxide, (a) soon after mixing, (b) after 20 min.

Fig. 2. Visible spectra in dimethyl sulphoxide of the 1 1 adducts of 2,4,6-trinitro-anisole formed (a) by addition of methoxide at Cl, (b) by addition of sulphite at C3.

Trinitrophenetole is prepared in a way similar in principle to that for trinitro-anisole ... 

Most of the chemistry of PA is determined by its acidic nature. It is a strong acid whose ionization constant of 1.6 x I0 (Ref 31) makes it comparable in acid strength to pyrophosphoric acid and trichloroaicetic acid. PA readily forms salts with bases and esters with alcohols. The salts are known as Picrates. Many of them are expl and will be described in a separate article in this Vol. The esters are phenol ethers, eg, Trinitro-anisole (see Vol 1, A450-L)... 

One nitro group of 0-dinitrobenzene and its derivatives is reactive and can be replaced by a mercapto, alkylthio, or sulfo group under the influence of sodium sulfide, sodium thiolates, or sodium sulfite, respectively. For preparative purposes this reaction is, however, restricted to a few examples. o-Dinitro-benzene and sodium sulfide give bis-(0-nitrophenyl) sulfide,492 and trinitro-anisole gives the bis(methoxydinitrophenyl) sulfide.493... 

Alkyl derivatives other than halides have been used to form pyridinium salts. Potassium ethyl sulphate gives the ethyl-pyridinium salt i and dimethyl sulphate is nd alkyl toluenesulphonates i quaternize pyridine. Primary and secondary alkyl nitrates and polymethylene dinitrates have also been used, but with t-butyl and cyclohexyl nitrate only elimination occurs320. 2,4,6-Trinitro-anisole and -phenetole convert pyridine into the alkylpyridinium picrates32i. 

Trinitro Methyl Anisole (4,6-Dinitro-2-nitro-methyl-anisole, 3,5-Dinitro-6-methoxy-nitro-methyl toluol or Methyl-[4,6-dinitro-2-nitro-methyl phenyl]-ether). CH3.0.(N02)2C H2.— CH2N02, mw 257.18, N 16.34%, OB to C02 —77.77%, cryst, mp 65—66°. Prepd from 4-nitro 2-(mtromethyl)anisole by slow addition to a mixt of coned sulfuric-nitric acids (2 1) at 0° (Ref 2). Explodes violently when heated quickly (Ref 2)... 

Tri nitrobutyl methyl anisole, c12H1sN307, mw 313.26, N 13.42%. Two isomers are described in the literature 2,4,6-TTinitro-5-(tert-butyl)-3 -methyl-anizole or 2,4,6-Trinitro-3-metboxy-5 -(tert-butyD-toluene. C4H. C6(NO2)3(CH3).0. ... 

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)... 

Trinitro-5 -chloro-3-hydroxy anisole or 3-Chloro-3-methoxy-picric Acid, nearly col micro-prisms(from w), mp 14 7° was prepd by adding lg of 5 -chloro-3-hydroxyanisole to well-stirred 10 ml of nitric acid(d 1.4 7) at RT during 15 mins, followed by slow heating to bp, cooling and pouring on ice. Itsexpl props were not detd... 

Chloromethoxy-picric Acid, See Trinitro-chlorohydroxyanisole under Chlorohydroxy-anisole... 

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) ... 

Trinitro-5-Methyl Anisole (2,4,6-Trinitro-3-methoxy-l-methyl-benzol or Methyl-[2,4,6-trinitro-S-methyl-phenyl] -ether). CH3.0.(N02)3CgH.CH3, mw 247.18, N 17.00%, OB to CO2 —80.91%, cryst, mp 92°, sol in conventional organic solvents (Ref 1). 

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