Methazonic Acid

Mercury Methazonate. See under Methazonic Acid in this Vol... 

Na hydroxide first forms the Na salt of NMe, then the Na salt of methazonic acid, and finally the Na salt of nitroacetic acid (Ref 10). 5) With Hg(ll) chloride is formed first the Hg salt of NMe which rearranges and dehydrates to MF (Ref 10). 

Methazonic Acid (Nitroacetaldoxime). C2H4N203, mw 104.07, N 26.92%, OB to C02 —46.12% leaflets from eth, prisms from benz and plates from chlf mp 79° (de-compn), bp (explds at 150°) sol in w, ale, eth, acet, warm benz and chlf. Can be prepd by heating nitromethane with ale NaOH or by treating nitromethane with aq ammonia at a temp below 10° (Refs 2, 3 4)... 

Methazonic acid is an exp], less powerful than TNT (Trauzl block expansion 240cc vs 290cc for TNT) but more sensitive to impact (comparable to PA). It is unstable in storage... 

Nitroacetaldoxime. See Methazonic Acid in Vol 1, A16-L, listed as Mononitroacetaldoxime under Acetaldoxime... 

The oxime (an isomer of ethylnitrolic acid ) decomposes gradually at ambient temperature, but explosively above 110°C [1], The product from treatment of nitromethane with strong sodium hydroxide solution at 50°C, followed by acidification and ether extraction, gave, after vacuum evaporation, a residue which exploded when air was admitted. On this occasion, a weekend elapsed between alkali and acid treatments, and it seems possible that formation of fulminic acid derivatives may have occurred [2], A 75 g sample of methazonic acid, from a preparation which had transiently overheated to 70°C, during the addition of nitromethane to sodium hydroxide solution, was stored for a week at — 15°C, then allowed to warm to room temperature. Twelve hours later it spontaneously detonated, destroying a fume hood. There is no evident cause for this explosion [3], It seems sensible to... 

The resulting bis-silylated derivative of methazonic acid contained the SENA fragment and, in the author s opinion, was produced by condensation of two... 

Two molecules condense with elimination of water to the so-called methazonic acid, which has the constitution of nitroacetaldoxine (I) (Meister).1... 

Coupling of aromatic diazonium salts with methazonic acid gives the oxime-hydrazones 79, which can be dehydrated by acid anhydride or acid chloride in alkali to 4-nitro-2/f-1,2,3-triazoles (80) (Scheme 18).70,71... 

Isatin has been reported to yield 3-nitrocinchoninic acid (92 R = C02H) with nitromethane in aqueous KOH.83 Although this seems like the use of a type 1 synthon, it is more appropriate to regard it as another example of a methazonic acid reaction. The reaction of nitroacetone with o-aminobenz-aldehyde leads to 2-methyl-3-nitroquinoline derivatives.84... 

H 20.09% ndl (chlf), dec 183°. Prepd from 4-nitroaniline and methazonic acid Refs l)Beil 12, 717 2)W.Meister,... 

Methazonic Acid (Nitroacetaldoxime). C2H4N2O3, mw 104.07, N 26.92%, OB to CO2 -46.12% leaflets from eth, CH2NO2 prisms from benz and plates... 

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