2-Nitro-4- resorcinol

Acetoxymercuri-2-nitroresorcinol is prepared by heating together equimoiecular quantities of mercuric acetate and 2-nitro-resorcinol on a water-bath for thirty minutes. The orange precipitate is filtered, Avashed with water, alcohol, and ether, then dried over ea]( ium chloride for forty-eight hours. Yield 75 per cent. 

Preparation by reaction of benzotrichloride with 2-nitro-resorcinol in hydrofluoric acid in the presence of water at -10° for 4 h, then at r.t. overnight (98%) [213]. 

Preparation by reaction of benzoic anhydride with 4-nitro-resorcinol in the presence of alumininm chloride in nitro-benzene on a steam bath for 3 h [1208]. 

Preparation by Fries rearranganent of 2-nitro-resorcinol dibenzoate with aluminium chloride in nitrobenzene at 100-110° for 3 h (40%) [1207]. 

Preparation by reaction of acetic anhydride on 2-nitro-resorcinol with aluminium chloride in nitrobenzene at 100° [2124,2125], (53%) [2124],... 

Polymers. AH nitro alcohols are sources of formaldehyde for cross-linking in polymers of urea, melamine, phenols, resorcinol, etc (see Amino RESINS AND PLASTICS). Nitrodiols and 2-hydroxymethyl-2-nitro-l,3-propanediol can be used as polyols to form polyester or polyurethane products (see Polyesters Urethane polymers). 2-Methyl-2-nitro-l-propanol is used in tires to promote the adhesion of mbber to tire cord (qv). Nitro alcohols are used as hardening agents in photographic processes, and 2-hydroxymethyl-2-nitro-l,3-propanediol is a cross-linking agent for starch adhesives, polyamides, urea resins, or wool, and in tanning operations (17—25). Wrinkle-resistant fabric with reduced free formaldehyde content is obtained by treatment with... 

Nitro-l-diazo-2-naphthol-4-sulfonic acid prefers the 2-position in spite of the nitro group, and increasing alkalinity favors ortho coupling with diazophenols. 1-Naphthalenesulfamic acid [24344-19-2] (ArNHSO H) and N-nitro-1-naphthylamine [4323-69-7] (ArNHNO ) couple exclusively in the para position. The substitution of resorcinol [108-46-3] and y -phenylenediamine [108-45-2] is compHcated and has been discussed (29,30). The first azo dyes from aniline, eg. Aniline Yellow [60-09-3] (19) (Cl Solvent Yellow 1 Cl 11000) were manufactured in 1861 and Bismark Brown [10114-58-6] (20) (Cl Basic Brown 1 Cl 21000) appeared in 1863. The reaction is as follows ... 

X 10mol/L). Both experiments were conducted at 25 °C. The decomposition rate of 4-nitro-aniline was very high by the photo-Fenton reaction in comparison to titanium dioxide-UV light (k = 365 nm). Decomposition products identified in both reactions were nitrobenzene, p-benzoquinone, hydroquinone, oxalic acid, and resorcinol. Oxalic acid, hydroquinone, and p-benzoquinone were identified as intermediate products using HPLC. 

The pH values of efficient extraction correspond to the pH range where the molecular form of the respective phenol dominates. The recovery of 4-nitro-phenol, 2,4-dinitrophenol, 2,6-dinitrophenol, 4-chlorophenol, 1-naphthol, and 2-naphthol is above 90% (the ratio of aqueous organic phase volume is 3 1). The extraction of naphthol and 4-chlorophenol is significant even at pH > pffa, more than 40 and 24% at pH > 10, respectively. Recovery of picric acid (2,4,6-trinitrophenol) is about 90% at pH 1.5-12.0, where the anionic form of picric acid dominates. Obviously, the high extraction is caused by high hydrophobicity of picrate anions. Recovery of the phenol itself and diatomic phenols, catechol and resorcinol is rather moderate (79,58, and 20%, respectively pH 1-7), which could be explained by relatively high hydrophi-licity of these compounds. 

As regards organic contaminants, leachates from semi-coke contain compounds such as phenols, for example, cresols, resorcinols, and xylenols, which occur at mg/L concentrations. Indeed, Kahru et al. (2002) found total phenols at concentrations up to 380 mg/L in semi-coke dump leachates. Phenols also volatilize from such leachates, depending on temperature and pH (Kundel Liblik 2000). Atmospheric phenol concentrations of 4-50 xg/m3 have been observed in the proximity of leachate ponds (Koel 1999). Generally, aliphatic hydrocarbons, carboxylic acids, and organo-nitro and organo-sulpho compounds do not occur at elevated concentrations in leachates from Estonian semi-coke (Koel 1999). 

The presence of nitro groups in phenol and resorcinol enhances their acidic properties and that is why trinitrophenol is commonly known as picric acid while trinitroresorcinol is known as styphnic acid. 

Resorcinol, 5-Methyl, 2,4,6-Trinitro (2,4,6-Tri-nitro-3,5-dioxy-l-methyl benzene or eso-Trinitro-Orcinol). (02N)3C6(OH)2.CH3 mw 259.15 ... 

Silica gel G MeOH NH3 (100 radiochromatog.. 67 65 1.5) Folin-Ciocalteau benzene iMieOH diazotized p-nitro-. 53 28 6NH3 (79 20 1)aniline, naphtha-resorcinol... 

The reaction occurs best at pH 11. The conversion to ammonia is 7% at PNa = 1 atm and 60% at PNz = 80 atm, and pyrocatechol is the best phenol phenol itself, resorcinol, and hydroquinone are inactive. More recently, it has been shown (232) that the stoichiometry is better represented as shown in Eq. (80). This is clearly similar to the currently accepted equation describing the stoichiometry of fixation by nitro-genase. 

Ready conversion of nitro compounds to amines further extends the applicability of the deamination process. For example, the nitro group may be introduced into an aromatic nucleus for the purpose of closing a position to other groups in subsequent steps of a synthetic sequence, and, finally, the nitro group is replaced by hydrogen. This blocking effect is utilized in the preparation of 2-chlororesorcinol, which cannot be obtained by direct chlorination of resorcinol.187... 

The method is used for those readily nitrated phenols (e.g. resorcinol), when less nitro groups are to be introduced than is possible in the direct nitration (Kosta-necki and Feinstein [205]). 

Among polyhydric phenols, only the nitro derivatives of resorcinol have gained considerable practical importance. The nitro derivatives of phloroglucinol may also be of some value. Both phenols have hydroxyl groups in the meta position to each other, thus enabling the introduction of three nitro groups. Among dinitro derivatives, those of pyrocatechol have found some uses. 

Among all the possible nitro derivatives of resorcinol only di- and tri-nitroresorci-nols are of practical value. Both are used as initiating explosives in the form of lead salts (Vol. III). The lead salt (Pb2+) of dinitroresorcinol is also of some practical value and in this connection some data characteristic of the compound will be given. 

Relationships between the structure and stability of phenol-starch complexes are not clearly understood. Apart from the complexes of phenols listed in Table XXXII, complexes of chlorocresols,712 three isomeric nitro-phenols,715 resorcinol, phloroglucinol, and rutin,716 have been reported. The formation of complexes with nitrophenols has been monitored by ultraviolet... 

Another interesting intermolecular reaction involving the phenoxenium ion 21 as supposed intermediate, was observed by reacting 20 with resorcinol-dimethylether to give 23 and 24 (61% and 13% yield by O—C or C—C-coupling, respectively some 2-nitro-4-phenoxyphenol (22) is also formed 207). 

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