4-diazo-2,6-dinitrophenol

Diazo-4,6-dinitrophenol (DDNP or DINOL) (53) can be prepared from the diazotization of 2-amino-4,6-dinitrophenol (52) (picramic acid) with nitrous acid " the latter is obtained from the selective reduction of picric acid with ammonium sulfide." 2-Diazo-4,6-dinitrophenol (53) is widely used as an initiating charge in detonators and caps. 

The nitration of both 4-methyl- and 4-chloro-2,6-dinitrotoluenes (66 and 67) with mixed acid in acetic acid at subambient temperature allows the isolation of the nitramines, (68) and (69), respectively. Thermolysis of (68) and (69) in refluxing methylene chloride yields the corresponding diazophenols, (70) and (71), respectively. Scilly and co-workers isolated 2-diazo-4,6-dinitrophenol (DINOL) (53) from the thermolysis of fV,2,3,5-tetranitroaniline (73) in ethyl acetate at 60 °C. 

In conventional ammunition lead, antimony, and barium are emitted when the ammunition is discharged. These three elements are undesirable from a health viewpoint and pose a major problem for firearms instructors in indoor firing ranges, as they are exposed to an unhealthy environment each working day. To solve this problem Dynamit Nobel AG developed a nontoxic primer composition called Sintox. Lead styphnate is replaced by 2-diazo-4,6-dinitrophenol (diazole) and the barium nitrate and antimony sulfide are replaced by a mixture of zinc peroxide and titanium metal powder. 

The 2-diazo-4,6-dinitrophenol (dinol, diazol, DDNP, DDNPh, or DADNPh) is the first-ever synthesized diazonium compound. Its synthesis is attributed to Griess [1] who prepared it by introducing nitric oxides into an alcoholic solution of 2-amino-4,6-dinitrophenol (picramic acid) [1,2]. Its explosive character was, however, first reported more than 30 years later in 1892 by Lenze [3]. 

Deflagration-to-detonation transition 2-Diazo-4,6-dinitrophenol 4,6-Dinitrobenzofuroxan Dinitroresorcinol 1,3-dihydroxybenzene Differential scanning calorimetry Differential thermal analysis Differential thermogravimetry Energy... 

C6H2(N02)30H (NH SaQs C02+HN03+HCN When mildly reduced, for example with Na sulfide or hydrosulfite or with ferrous sulfate, PA is converted into picramic acid, a very useful intermediate in the dyestuffs industry and a starting material for the preparation of Diazo-dinitrophenol, a primary expl (see Vol 2, B59-L). Stronger reduction may lead to the formation of triamino phenol... 

As already mentioned, MF was largely (and now wholly) displaced since 1930 by LA (Lead Azide) and also by DAzDNPh (Diazo-dinitrophenol), Cyanuric Triazide and LSt (Lead Styphnate). This took place first in... 

High Explosive Mercury Fulminate Diazo- dinitrophenol Lead Azi... 

The procedure of simultaneous extracting-spectrophotometric determination of nitrophenols in wastewater is proposed on the example of the analysis of mixtures of mono-, di-, and trinitrophenols. The procedure consists of extraction concentrating in an acid medium, and sequential back-extractions under various pH. Such procedures give possibility for isolation o-, m-, p-nitrophenols, a-, P-, y-dinitrophenols and trinitrophenol in separate groups. Simultaneous determination is carried out by summary light-absorption of nitrophenol-ions. The error of determination concentrations on maximum contaminant level in natural waters doesn t exceed 10%. The peculiarities of application of the sequential extractions under fixed pH were studied on the example of mixture of simplest phenols (phenol, o-, m-, />-cresols). The procedure of their determination is based on the extraction to carbon tetrachloride, subsequent back-extraction and spectrophotometric measurement of interaction products with diazo-p-nitroaniline. 

Calculations on the 4-aminobenzenediazonium ion were also carried out by Alcock et al. (1980a) using ab initio and MINDO/3 techniques. They came to the conclusion that both methods have poor predictive value for the geometry of an ion of such complexity. However, two other semiempirical methods, namely MNDO (Dewar and Thiel, 1977) and AM-1 (Dewar et al., 1985), were applied with better results to a similar, but even more complex, zwitterionic diazo compound, 2-diazonio-4,6-dinitrophenolate, by Lowe-Ma et al. (1988 see 4.4 in Sec. 4.2). 

Shortly after Perkin had produced the first commercially successful dyestuff, a discovery was made which led to what is now the dominant chemical class of dyestuffs, the azo dyes. This development stemmed from the work of Peter Griess, who in 1858 passed nitrous fumes (which correspond to the formula N203) into a cold alcoholic solution of 2-aminO 4,6 dinitrophenol (picramic acid) and isolated a cationic product, the properties of which showed it to be a member of a new class of compounds [1]. Griess extended his investigations to other primary aromatic amines and showed his reaction to be generally applicable. He named the products diazo compounds and the reaction came to be known as the diazotisation reaction. This reaction can be represented most simply by Scheme 4.1, in which HX stands for a strong monobasic acid and Ar is any aromatic or heteroaromatic nucleus. 

The nitration of 2-amino-4,6-dinitrotoluene (63) with a mixtnre of nitric acid in sulfuric and acetic acids yields 2-diazo-3-methyl-4,6-dinitrophenol (65) in 75 % yield without isolation of the intermediate nitramine (64)." ... 

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