2- Nitro 2,7-Dinitro

This change in editorial leadership has resulted, perhaps inevitably, in a change in editorial policy which is reflected in the contents of Volume 8. There has been a marked de-emphasis on the inclusion of organic parent compounds followed by an exhaustive and voluminous cataloging of azide, azido, azo, diazido, diazonium, diazo, nitro, dinitro, polynitro, hitr amine, nitrate (esters and salts), dinitrate, poly nitrate, nitroso, polynitroso, chlorate, perchlorate, peroxide, picrate, etc, derivatives — regardless of whether any of these derivatives exhibit documented explosive or energetic properties. Only those materials having such properties have been included in this volume... 

Of 9.64 kcal/mol. Isomers in which acetyl group is attached to the ring, anilinoaceto phenones, are not described in Beil, although their nitro-, dinitro- and trinitro derivs are listed in vol 14. One of the anilinoaceto-phenones, was prepd recently by S.G.P.Plant C.R. Worthing, JCS 1955,1279 CA 50, 2457(1956) and listed as 4-acetyldiphenyl-amine... 

No azido-, diazido-, nitro-, dinitro-, etc derivs of azoaniline were found in Beit or CA through 1956, but there exist nitrated compds of diaminoazobenzenes... 

Oiah H.C. Lin, Aromatic Substitution. .. Selectivity of the Nitration of Nitro (Dinitro)... 

Azoxyethane, C2HS (N20) C2H5, as well as its Azido, Diazido, Nitro, Dinitro, Nitroso,... 

Nitro-, Dinitro- and Trinitro-diphenylamines ate known and ate listed in Vol 1 of Encycl, p A443 under Anilinoxylenes and Derivatives. None of these compds seems to be explosive... 

Theoretical calculation of a + n electronic structure of nitrobenzenes and nitrotoluenes were carried out by LCAO method and gave a good agreement with electronic spectra and dipole moments [22]. Later the CNDO and ab ittitio calculation for nitro-, dinitro- and trinitrobenzenes gave a very good agreement with spectral features and dipole moments [23]. 

Anthraquinone can be brominated, chlorinated directly to the tetrachloro (I, 4, 5, 8-) stage, nitrated easily in the 1-position, but gives the 1,5-and 1,8-dinitro-derivalives on prolonged nitration the nitro groups in these compounds are easily displaced by neutral solutions of alkali sulphites yielding the corresponding sulphonic acids. Sulphonation with 20-30 % oleum gives the 2- 2,6- and 2,7-derivatives in the presence of Hg the 1- 1,5- and 1,8- derivatives are formed. 

Can be coupled in the 4-position with dia-zotized bases to give a series of azo dyestuffs more usually it is first sulphonated to give a valuable series of intermediates for solubilized azo dyestuffs. The nitro-l-naphthols are themselves dyestuffs, e.g. 2,4-dinitro-l-naph-thol ( naphtol yellow ). 

Yellow. Quinones, m- and p-nitroaniline, o-nitrophenol, and many other nitrO"Compounds. [Note that some nitro-compounds often appear yellow (e.g. m-dinitrobenzene and 3, 5 -dinitro-benzoic acid), but are colourless when absolutely pure.] Iodoform. 

Amine B.P. M.P. Aceta- mide Benz- amlde Benzene- SUlphOD- amlde p-Tolu- enesul- phoD- amlde Benzal Derivative Picrate 3-Nitro- phthal- imide 2 4-Dinitro-phenyl Derivative Formyl Derivative Phenyl thio- urea... 

Alcohol B.P. M.P, 3 5-Dinitro-benzoate p-Nilro- bemoate Phenyl- urethane a-Naph- thyl- urethane Hydrogen 3-nitro- phthalate other Derivatives... 

The nitration of nitro- and dinitro-biphenyls has been examined by several workers. i - As would be expected, nitration of the nitro-biphenyls occurs in the phenyl ring. Like a phenyl group, a nitrophenyl group is 0 -directing, but like certain substituents of the type CH CHA ( 9.1.6) it is, except in the case of w-nitrophenyl, deactivating. Partial rate factors for the nitration at o °C of biphenyl and the nitro-biphenyls with solutions prepared from nitric acid and acetic anhydride are given below. The high o p-v2X o found for nitration of biphenyl... 

Naphthalenol also is used ia the preparation of azo, iadigoid, and nitro, eg, 2,4-dinitro-l-naphthol, dyes, and ia making dye iatermediates, eg, naphtholsulfonic acids, 4-chloro-1-naphthalenol, and l-hydroxy-2-naphthoic acid. 1-Naphthalenol is an antioxidant for gasoline, and some of its alkylated derivatives are stabilizers for plastics and mbber (68). 

In additionto the mononitro compounds, monohydric and dihydric dinitro alcohols have been prepared but are not available commercially. The formation, properties, and reactions of nitro alcohols have been reviewed (1,2). 

Most nitroparaffins do not react with ketones, but ia the presence of alkoxide catalysts, nitromethane and lower aUphatic ketones give nitro alcohols ia the presence of amine catalysts dinitro compounds are obtained. 

I itro-DisplacementPolymerization. The facile nucleophilic displacement of a nitro group on a phthalimide by an oxyanion has been used to prepare polyetherimides by heating bisphenoxides with bisnitrophthalimides (91). For example with 4,4 -dinitro monomers, a polymer with the Ultem backbone is prepared as follows (92). Because of the high reactivity of the nitro phthalimides, the polymerkation can be carried out at temperatures below 75°C. Relative reactivities are nitro compounds over halogens, Ai-aryl imides over A/-alkyl imides, and 3-substituents over 4-substituents. Solvents are usually dipolar aprotic Hquids such as dimethyl sulfoxide, and sometimes an aromatic Hquid is used, in addition. 

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