Synthesis of methazonic acid

Preparation of methazonic acid

Preparation of methazonic acid

Preparation of methazonic acid

Synthesis of methazonic acid 45 grams of nitromethane is prepared within a 500ml flask. Along with this, 40 grams of sodium hydroxide in 18 grams of water is prepared. The mixture is warmed to 50 degrees, and  the sodium hydroxide is added over a period of 1 hour under constant temperature management (sodium hydroxide has a strong exotherm.) After this, the mixture is cooled to 0 degrees in an ice bath, and 35 grams of 37% hydrochloric acid is added, keeping the temperature between 0-5 degrees. The resulting yellow solid is filtered and dried in a Buchner under a vacuum for an hour. This is then dissolved in diethyl ether and dried over anhydrous calcium chloride. The drying agent is then filtered and the diethyl ether evaporated to dryness, yielding 46 grams of methazonic acid. The methazonic acid synthesized can then be reacted with any metal hydroxide to form the metal methazonate salt. Small amounts of methazonic acid reacted with potassium hydroxide yield potassium methazonate, a highly sensitive primary explosive. The transition metal salts are presumed to be even more brisant and sensitive. Under no circumstances should methazonic acid be reacted with any ammonium salts: ammonium methazonate readily decomposes, producing extremely toxic hydrogen cyanide gas.

J. Org. Chem 1960,25, 266-268

IUPAC Name

(NE)-N-(2-nitroethylidene)hydroxylamine

InChI

InChI=1S/C2H4N2O3/c5-3-1-2-4(6)7/h1,5H,2H2/b3-1+

InChI Key

FYFYCAVDUPOEOO-HNQUOIGGSA-N

Canonical SMILES

C(C=NO)[N+](=O)[O-]

Isomeric SMILES

C(/C=N/O)[N+](=O)[O-]

Depositor-Supplied Synonyms

5653-21-4, 2-NITROACETALDEHYDE OXIME, Methazoic acid, 2-nitroacetaldoxime, Nitroacetaldehyde oxime, Methazoic acid [Forbidden], Acetaldehyde, nitro-, oxime, SCHEMBL1423672, AKOS022182666, AK-72655, (E)-N-(2-nitro-ethylidene)-hydroxylamine

Removed Synonyms

ACETALDEHYDE,NITRO-,OXIME

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