Tetrazen tetrazene

The reaction of aminoguanidine with sodium nitrite under neutral conditions yields tetra-zolylguanyltetrazene hydrate (85), a primary explosive commonly known as tetrazene. Tetrazene (85) is only formed in the absence of free mineral acid and so a common method for its preparation treats the bicarbonate salt of aminoguanidine (84) with one equivalent of acetic acid followed by addition of aqueous sodium nitrite. " Tetrazene (85) is decomposed by aqueous alkali to form triazonitrosoaminoguanidine (86) which is isolated as the cuprate salt (87) on addition of copper acetate to the reaction mixture. Acidification of the copper salt (87) with mineral acid leads to the formation of 5-azidotetrazole (88) (CHN7 = 88 % N).55 56... 

Tetrazene (Tetrazen in Ger) is a collective name for derivatives of compds contg 4 nitrogens in a straight chain, such as Tetrazene (1),... 

Tetrazene. Tetrazene, 14, is classified as a primary explosive that is a very hazardous material. An explosion can occur during the preparation that is based on sodium nitrite and amino guanidine sulfate (15). 

Tetrazene (Tetrazen in Ger) is a collective name for derivatives of compds contg 4 nitrogens in a straight chain, such as Tetrazene (1), R.N N.NH.N R.R, and Tetrazene (2), R.R N.N N.N R.R, where R is any alkyl or aryl radical Tetrazenes (1) were formerly called Diazo-hydrazides by Wohl and Schiff (Ref 3), while Tetrazenes (2) were called Tetrazenes" by Fischer (Ref 2)... 

Tetrazene. Tetrazene or tetrazolyl guanyltetrazene hydrate (C2H6Nio-H20) (2.5) was first prepared by Hoffmann and Roth in 1910 by the action of a neutral solution of sodium nitrite on... 

Property Mercury fiihninate Lead azide Silver azide Normal lead styphnate DDNP Tetrazene... 

Solutions of colourless pyrazolidinediones give highly coloured solutions of radicals (113) when treated with lead dioxide. The ESR spectra of these radicals have been recorded (78JOC808). They dimerize to tetrazenes (114) which appear to be indefinitely stable. 

Hetero Diels-Alder reaction of active olefins (enamines) with triazenes, tetrazenes with loss of Nz and formation of new N-heterocycies. 

N4H4 rra 5-2-tetrazene, H2N-N=N-NH2, (colourless, low-melting ciystals, N-N 143pm, N=N 121pm). and ammonium azide, NH4N3 (white ciystals, subl. 133°C, d 1.350gcm 3)... 

Uses It can be used as a secondary charge in detonators replacing Tetryl. Mixts with Diaz onitrophenol (Encycl 2, B59) or Tetrazene... 

C6H4Br.N N.N(C6Hs).N N.N(C6Hs).N N.C6H4Br, pale yel substance, mp 60°. Can be prepd by treating a cold ethereal soln of 3-phenyl-l-[4-bromphenyl]-tetrazene-(l) with a 1% soln of K permanganate (Refl). It is an expl... 

Expls may be classified both from the chemical point of view and according to their uses. From the chemical viewpoint we distinguish between chemical individual substances and mixts. The former are divided into (1) nitro compds, (2) nitric esters, (3) nitramines, (4) derivatives of chloric and perchloric acids, (5) azides, and (6) various compds capable of pro-during an expln, for example fulminates, acetyl-ides, nitrogen rich compds such as tetrazene, peroxides and ozonides, etc... 

Compounds with the classical nonsystematic name diazoamino compound (R-N2NRiR2) and their (logical) derivatives with two or more adjacent nitrogen atoms are considered as substitution products of triazene (NH2 — N=NH), 1-tetrazene, etc. (Rule 942.1). Simple examples are 3-methyltriazene (CH3-NH-N = NH) and 3-methyl-l-tetrazene [NH2-N(CH3)-N = NH]. The classical name is retained only for compounds containing the same group R at each end of an - N=N - NH - group (Rule C-942.2), e. g., A-methyldiazoaminobenzene,... 

In contrast to the addition products of hydrazines, the interaction of arenediazonium ions with acid hydrazides (Scheme 6-18) yields tetrazenes (6.26), which can be isolated. Tetrazoles (6.27) are obtainable by cyclization (Dimroth and de Mont-mollin, 1910). 

Triazene lassen sich durch Lithiumalanat nicht reduzieren3. Tetramethyl-tetrazen liefert mit Trimethyl-amin-alurninium-hydrid Dimethylamino-aluminium-hydrid und Trimethylamin, ... 

Keywords Valence electron rule, Metal ring, Metal cluster, AN +2 valence electron rule, 8/V +6 valence electron rule, 6N +14 valence electron rule, Pentagon stability, Cyclopentaphosphane, Hydronitrogen, Polynitrogen, Triazene, 2-Tetrazene, Tetrazadiene, Pentazole, Hexazine, Nitrogen Oxide, Disiloxane, Disilaoxirane, 1,3-Cyclodisiloxane, Metallacycle, Inorganic heterocycle... 

The delocalization of lone pair electrons on NH group to an adjacent N=N bond was suggested by some calculations [97] to be appreciable in triazene 12 and 2-tetrazene 13. The N-N single bond is shorter than the isolated N-N single bond in NH NH. The N=N bond is longer than in NH=NH. The n-n conjngation stabilizes hydronitrogens. 

Diazonium salts add to active methylene compounds, for example ethyl acetoacetate, to form an intermediate azo compound (22), followed by the addition of a second diazonium salt (under more alkaline conditions) to yield the tetrazene (23) which then forms a 3-substituted formazan (24)10... 

Disubstituted tetrazoles are conveniently prepared from acyl hydrazines (98) and diazonium salts.166 The reaction proceeds through the intermediate tetrazenes (99) followed by cyclization to the tetrazole (100) (Scheme 13). The intermediate can be isolated under mildly basic conditions. Symmetrically 1,2-diacylated hydrazines yield 1-substituted tetrazoles through the elimination of one of the acyl groups.166 - 168 Diformyl-hydrazine is a very convenient starting material for 1-substituted tetrazoles.166, Unsymmetrically 1,2-diacylated hydrazine usually results in mixtures.169... 

Diazonium salts react with bis(methylsulfonyl) methane (107) (X = S02CH3) to yield a 1,3-diaryl tetrazolinone (111). The reaction proceeds through an azo (108) and a tetrazene (109) intermediate, followed by hydrolysis under the alkaline conditions of the reaction to the carbonyl compound (110). An unexplained oxidation leads to the 1,3-diaryl tetrazolinone (111) either directly or through the intermediate 110a (Scheme 15).18,35 A similar reaction occurs between a diazonium salt and the potassium salt of phenyl hydrazonomethane disulfonic acid (Scheme 15).175... 

Tetrazene was discovered by Hofmann and Roth in 1910 and the structure determined by Duke. It is made by the action of sodium nitrite on aminoguanidine sulphate or nitrate under slightly acid conditions. 

Tetrazene is a light yellow crystalline substance, insoluble in water and most organic solvents. The density is low under normal conditions, but on pressing can reach approximately 1 g ml-1. Tetrazene is weak as an initiating explosive, and is therefore not used alone. It has no advantages to commend it for use in commercial detonators, but does find application in the manufacture of military and other percussion caps. Like diazodinitrophenol, tetrazene does not detonate when ignited in the open, but only when ignited under confinement. 

See other perchlorate salts of nitrogenous bases, tetrazenes... 

See other high-nitrogen compounds, tetrazenes, tetrazoles... 

---