Tetra nitromethane

N 28.85% wh crysrs (from chlf), mp 94-96° decomposes rapidly above its mp, d 1.91 at 20° was first synthesized by German scientists (Ref 2) can be prepd by reacting tetra-nitromethane with NH in the presence of H C, the resulting ammonium nitroform is then treated with formaldehyde (Ref 3)... 

COj -48.5%, OB to CO -12.1%. Plates, unstable, mp 55 62° with decompn very sol in w eth, in sol in ligioin. Was prepd by mixing acetone with nitric acid(dl. 14) and a little fuming HNO, and allowing the mixt to stand for 8 days at RT. An ether extraction gave on e-apcm seme acstylmethyi-nitrolic acid(Refs 1 2). Krauz Stepanek (Ref 3) attempted and failed to prep tetra-nitromethane by nitration of acet. Instead, they obtd (after treating the nitrated prod with silver salt) an expl compd claimed to be the Ag salt of acetylmethylnitrolic acid, CHj, , CO. C(NOj). N. 0 Ag (see also Acetone, Nitration)... 

EXTENSIONS AND COMMENTARY This is pretty sparse information upon which to build a picture of biological activity. First, the synthesis was done by someone else and, as I have not been able to find where the notes are, this will be the one recipe in the footnote without explicit directions incorporated. The procedure used was exactly the same as that described for DMMDA, except that the starting material was dillapiole rather than apiole. The dillapiole was obtained by the careful fractionation of Oil of Dill (as opposed to the isolation of apiole from the careful fractionation of Oil of Parsley). Isomerization to isodillapiole, nitration with tetra-nitromethane to give 1 -(2,3-dimethoxy-4,5-methylenedioxyphenyl)-2-nitropropene, and its reduction with LAH in ether to give 2,3-dimethoxy-4,5-methylenedioxyamphetamine hydrochloride (DMMDA-2) proceeded in a precisely analogous manner to the preparation of DMMDA. 

Mixtures of aluminium powder with liquid chlorine, dinitrogen tetraoxide or tetra-nitromethane are detonable explosives, but not as powerful as aluminium—liquid oxygen mixtures, some of which exceed TNT in effect by a factor of 3 to 4 [1], Mixtures of the powdered metal and various bromates may explode on impact, heating or friction. Iodates and chlorates act similarly [2]. Detonation properties of gelled slurries of aluminium powder in aqueous nitrate or perchlorate salt solutions have been studied [3]. Reactions of aluminium powder with potassium chlorate or potassium perchlorate have been studied by thermal analysis [4],... 

Use of Carbon-14 to Study the Origin of Tetra-nitromethane (TeNMe) in TNT Manufacture. 

Treatment of thietane with electron acceptors, such as tetracyanoquino-dimethane (TCNQ), tetracyanoethylene (TCNE), maleic anhydride, or tetra-nitromethane, induces polymerization, believed to occur through an intermediate charge-transfer complex. The reaction with tetranitromethane is unusual because nitric oxide, nitrogen dioxide, carbon monoxide, ethylene, ethane, and propane are... 

It has been found by Crawford that small quantities of tetra nitromethane and nitrochloromethanes are frequently present in nitrx iyceriae. and depress the heat test. They may removed by shaking with sodium sulphite solution. 

Forman and Fridovich (1973) using an indirect assay whereby O2 was generated either by the action of xanthine oxidase on xanthine or by the mechanical infusion of potassium superoxide in tetrahydrofuran. The generated OJ was allowed to react with ferricytochrome c or with tetra-nitromethane and the product formation was monitored spectroscopically. Details of the two assays are given in Section 11.3. Addition of superoxide dismutase inhibits the formation of products. A rate constant of 2 X 10 M sec was determined for all three enzymes. This value agreed with the rate constant determined by pulse radiolysis for the copper/zinc enzyme (Klug-Roth et al., 1973 Fielden et al., 1974). The mechanism of action of the superoxide dismutases has been investigated by the technique of pulse radiolysis which is described in Section II.2. The bovine erythrocyte copper/zinc enzyme is the most studied form as far as the molecular and catalytic properties are concerned (Rotilio and Fielden,... 

One of the earliest observations of this phenomenon was made by Henglein and co-workers working with nitromethane solutions (11). In alkaline solutions the radical anion, CH8N02", absorbs at 2700 A. (e = 1800M 1 cm.1"). In the presence of a much lower concentration of tetra-nitromethane, electron transfer from CH3N02 was indicated by the buildup at 3500 A. of an absorption assigned to the radical ion C(N02). T... 

Isomerization to isodillapiole, nitration with tetra-nitromethane to give 1 -(2,3-dimethoxy-4,5-methylenedioxyphenyl)-2-nitropropene, and its reduction with LAH in ether to give... 

Glutathione S-transferases are susceptible to inactivation by reactive nitrogen species. Treatment of isolated glutathione S-transferases or rat liver homogenates with either peroxynitrite, the myeloper-oxidase/hydrogen peroxide/nitrite system, or tetra-nitromethane, resulted in loss of glutathione S-transferase activity with a concomitant increase in the formation of protein-associated 3-nitrotyrosine (Wong et al. 2001). 

Teuwissen, B.. P. L. Masson, P. Osinski, and J. F. Hermans Metal-combining Properties of Human Lactoferritin. Effect of Nitration of Lactoferritin with Tetra-nitromethane. Eur. J. Biochem. 35, 366-371 (1973). 

---