FLUORODINITROMETHYL

Metal Fulminates or aci - nitro salts Fluorodinitromethyl compounds... 

See entry FLUORODINITROMETHYL COMPOUNDS See Other POLYNITROALKYL COMPOUNDS... 

Outstandingly explosive among fluorodinitromethyl compounds, samples stored neat at ambient temperatures regularly exploded within a few horns. Occasionally, concentrated solutions in dichloromethane have decomposed violently after long storage. 

See also endothermic compounds, fluorodinitromethyl compounds (reference 6)... 

Fluoro-2,2-dinitroethanol, 0750 2-Fluoro-2,2-dinitroethylamine, 0800 Fluorodinitromethane, 0374 Fluorodinitromethyl azide, 0341... 

Fluoro-2,2-dinitroethanol, the methylol derivative of fluorodinitromethane, has been used extensively for the synthesis of fluorodinitromethyl compounds. The fluorine atom is similar in size to that of a proton and so rotation in the fluorodinitromethyl group is much less hindered compared to the trinitromethyl group. Consequently, these compounds are far less sensitive to impact than trinitromethyl compounds but only slightly less energetic. The explosive performance of fluorodinitromethyl compounds has been reviewed. ... 

A large number of nitramine-based explosives have been synthesized via Mannich-type condensation reactions (Section 5.13.2). The amines generated from these reactions often have the powerful electron-withdrawing trinitromethyl or fluorodinitromethyl groups positioned on the carbon a to the amino group. This reduces amine basicity to an extent that A-nitration becomes facile. The energetic nitramines (17), (19) and (21) have been synthesized from the condensation of ethylenediamine with 2,2,2-trinitroethanol, 2-fluoro-2,2-dinitroethanol with ethanolamine, and 2-fluoro-2,2-dinitroethylamine with 2,2-dinitro-l,3-propanediol respectively, followed by A-nitration of the resulting amine bases (16), (18) and (20), respectively. 

The azidoalcohols (20) and (21) have been reacted with acid chlorides and alkyl chloride to give esters containing both azido and fluorodinitromethyl functionality. ... 

A -(2-Fluoro-2,2-dinitroethyl)hydroxylamine (1) is oxidized by 3-chloroperoxybenzoic acid or bromine to afford oxime 2.218 This compound is unstable and over the course of several weeks at ambient temperature it rearranges quantitatively to amide 3.218 Further oxidation of the oxime 2 with nitric acid or aqueous chromic acid gives a product mixture, from which bis(fluorodinitromethyl)furoxane 4 is isolated.218... 

It is a potentially explosive vesicant, from which a series of esters, expected to be explosive, was prepared [1], During concentration of a dichloromethane solution, there is a sensitivity maximum between 30% solution and the pure compound [2]. See other FLUORODINITROMETHYL COMPOUNDS, POLYNITROALKYL COMPOUNDS... 

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