4- Hydroxy-3-nitrobenzene

Synonyms AI3-04856 AIDS-19393 C-00870 BRN 1281877 Caswell No. 603 CCRIS 2316 EINECS 202-811-7 EPA pesticide chemical code 056301 4-Hydroxynitrobenzene p-Hydroxy-nitrobenzene NCI-C55992 4-Nitro-l-hydroxybenzene p-Nitrophenol NSC 1317 PNP RCRA waste number U170 UN 1663. 

SYNS m-HYDROXYNITROBENZENE 3-HYDROXY-NITROBENZENE m-NITROFENOL m-NITRO-PHENOL (DO-p... 

SYNONYMS 4-Hydroxy nitrobenzene, niphen, nitrophenol, p-nitrophenol. 

Ha.loisoquinolines, The Sandmeyer reaction is commonly used to prepare chloroisoquinolines from the amino compound. The corresponding hydroxy compounds are also used by treatment with chlorides of phosphoms. The addition of bromine to a slurry of isoquinoline hydrochloride in nitrobenzene gives a 70—80% yield of 4-bromoisoquinoline [1532-97-4J. Heating 1-chloroisoquinoline [19493-44-8] with sodium iodide andhydriodic acid gives 1-iodoisoquinoline [19658-77-6] (179). 

Until recent years the only syntheses of 3-hydroxy quinoline involved multistep processes, the last step of which consisted of the conversion of 3-aminoquinoline to 3-hydroxyquinoline via the diazonium salt. " Small quantities of quinoline have been oxidized to 3-hydroxyquinoline in low yields by using oxygen in the presence of ascorbic acid, ethylenediaminetetraacetic acid, ferrous sulfate, and i)hosi)halc buffer. The decarboxylation of 3-hydroxycinchoninic, acid in boiling nitrobenzene has been re-... 

In contrast, o-(2-cyano-A-methylacetamido)nitrobenzene (38) gave 1-hydroxy-4-methyl-2,3(lH,4/7)-quinoxalinedione (40), presumably by hydrolysis of the intermediate carbonitrile (39) (NaOH, H2O, reflux, 30 min 53% or EtONa, EtOH, reflux, 30 min, aqueous workup 69%). " ... 

Treatment of suberin with nitrobenzene generates vanillin, p-hydroxy benz-aldehyde, but not much syringaldehyde that arises mostly from lignin. 

Alkaline Nitrobenzene Oxidation of Cornstalks. Isolation of p-Hydroxy-benzaldehyde. J. Amer. chem. Soc. 66, 37 (1944). 

Acid- and base-promoted methods have also been used in the syntheses of pyrazoles. Hydrogenation of methyl 2-Cbz(hydrazine)-3-hydroxy-4,4-dimethoxybutanoate 11 followed by cyclization in the presence of trifluoroacetic acid afforded the first asymmetric synthesis of the (4S,5.R)-5-carbomethoxy-4-hydroxy-A2-pyrazoline 12 <00TL8795>. Reaction of 2-nitrobenzyl triphenylphosphonium ylide (13) with aiyl isocyanates afforded 2-aryl-2H-indazoles 14 <00TL9893>. Base-promoted reaction of nitrobenzenes 15 with aryl imines 16 afforded aryl pyrazoles 17 . 

In the sulphonation of aniline small amounts of the o-compound are produced along with sulphanilic acid. Aniline o-sulphonic acid, however, is of no further interest. Metanilic acid, on the other hand, is also manufactured as an intermediate in the azo-dye industry. It is obtained from nitrobenzene-m-sulphonic acid by reduction. The amino-(iand hydroxy-) sulphonic adds of the naphthalene series are of the greatest technical importance. They are either diazotised themselves or serve for coupling with other diazo-compounds. In this way the most important azo-dyes are produced. 

The quantum yield for formation of 20, R=6-C(CH3)3, from 14, R=4-C(CH3)3, via photolysis in fer -butyl alcohol and oxidative workup, has been determined as (1.2 0.1) X 10 2 4 ). Quantum yields for formation of various other N-hydroxy-2-indolinones from appropriately substituted 2-nitro-fer -butylben-zenes fall into the range 1.1 X 10 to 2.2 X 10 and thus are of the same order of magnitude as the disappearance quantum yield reported for nitrobenzene in 2-propanol... 

Deprotonation provides the necessary electron push to kick out the electron pair joining C(6) with the nitrobenzene oxygen. If, however, N(l) is alkylated (as with the nucleosides and nucleotides), OH catalysis is much less efficient since it now proceeds by deprotonation from N(3) (with the uracils) or from the amino group at C(4) (with the cytosines). In these cases the area of deprotonation is separated from the reaction site by a (hydroxy)methylene group which means that the increase in electron density that results from deprotonation at N(3) is transferable to the reaction site only through the carbon skeleton (inductive effect), which is of course inefficient as compared to the electron-pair donation from N(l) (mesomeric effect) [26]. Reaction 15 is a 1 1 model for the catalytic effect of OH on the heterolysis of peroxyl radicals from pyrimidine-6-yl radicals (see Sect. 2.4). 

CASRN 15457-05-3 molecular formula C13H7F3N2O5 FW 328.20 Chemical/Physical. When fluorodifen as an aqueous suspension was irradiated using UV light (A, = 300 nm), 4-nitrophenol and 4-(trifluoromethyl)-2-aminophenol formed as the major products (>90% of total product formation). In addition, 4-(trifluoromethyl)-2-nitrophenol formed as a minor product (<1%) as well as 4-hydroxy-3-nitrobenzoic acid. In methanol, photolysis of fluorodifen yielded 4-nitrophenol and 2-amino-4-(trifluoromethyl)anisole. In cyclohexanone, 4-nitrophenol and 3-(trifluoromethyl)nitrobenzene were formed (Ruzo et al., 1980). 

Chlorpromazine and other phenothiazines can be identified by their reactions with benzene-, toluene-o-, and toluene /j-stilbinic acids, and with p-hydroxy-, m-nitro-, w-amino-, and p-nitrobenzene stilbinic acids in an HCl medium. The reaction products are initially colorless masses but rapidly oxidize to yield colored products [32]. 

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