4- Nitro-2-methylphenol

Using 2,6-diformyl-4-methylphenol dioxime, Tasker, Schroder, and their co-workers conducted a magnetostructural study on complex (374) (pseudo macrocyclic structure Cu-Cu 2.994 A 2J= — 904 cm-1).330 Using 2-hydroxy-5-nitro-benzaldehyde benzoylhydrazone as ligand, complex (375) (Cu-Cu 3.041 A 2J=—372cm 1) was reported.331 Using 3-formylsalicylic acid oxime Okawa and co-workers reported complex (376) (square-planar and SP geometry Cu-Cu 2.961 A).332... 

Amino-3-methylphenol, see 4-Nitrophenol Aminomethylphosphonic acid, see Glvnhosate 2 -Amino-2-naphthoxypropiophenone, see Napropamide 4-Amino-2-naphthoxypropiophenone, see Napropamide Aminonitrobenzoic acid, 3.4-Dinitrobenzoic acid 4-Amino-4 -nitrobiphenyl, see Benzidine 2-Amino-6-nitro-lV-(l-ethylpropyl)-3,4-xylidine, see... 

The direct nitration of m-cresol is unsatisfactory for obtaining 4-nitro-3-methylphenol (29%). A better procedure is to form the nitroso compound and oxidize it to the nitro compound (66% over-all). ... 

C7H6N204 3-(5-nitro-2-furyl)-2-propenamide 710-25-8 584.86 52.094 2 10522 C7H7CIO 4-chloro-2-methylphenol 1570-64-5 496.15 43.514 1,2... 

The effect of a nitro group is clearly diminished when the nitro group is twisted out of the ring plane, as seen by a comparison of 2-nitrophenol and 2-nitro-3-methylphenol. The compound 3-hydroxy-9-fluorenone shows an OH chemical shift of 92.5 ppm. This again can be related to the effects of the C=0 group, possibly in conjunction with a formal biphenyl moiety. 

Beilstein Handbook Reference) 4-Hydroxy-3-nitrotoluene AI3-15389 BRN 1868022 EINECS 204-3106 NSC 5387 2-Nitro-4-cresol 2-Nitro-p-cresol 2-Nitto-4-methylphenol 0-Nitro-p-cresol pCresol, 2-nitro-. Yellow needles mp = 36.5° bp = 125° d = 1.2399 very soluble in Me2CO, CeHe, EtzO, EtOH. 

The tert-butoxy radical is liberated by photolysis of XXXVIa (Scheme 9). Its formation was confirmed by reactions which produce more stable radicals detectable by the ESR method135. The heptane solution of XXXVIa was irradiated by light 360—480 nm in the presence of 2,6-di-tert-butyl-4-methylphenol or 2,4,6-tri-tert-butylphenol. These sterically hindered phenols were transformed by the liberated tert-butoxyl into phenoxyls. Their identification by the ESR method is the indirect evidence of tert-BuO formation. The direct evidence was achieved by means of nitro-sobenzene CVI (R=H) and nitrosodurene CVI (R=Me) as spin-traps. The nitroxide radical CVII (R=H or Me) is formed in both cases and was identified by ESR spectrum135. This spin-adduct is unstable. The intensity of its spectrum gradually decreases during irradiation and the spectrum of another radical appears which is less intense but invariable in time. Judging from its hyperfine structure, it may be formulated as CVIII (R=H or Me). More detailed data on the character of substituents RJ-R2 is not yet known. 

For the formation of nitro derivatives mild conditions are essential to avoid replacement of the branched alkyl group (ref. 88). The nitration of 6-tert-butyl-3-methylphenol and methylation of the product 6-tert-butyl-2,4-dinitro-3-methylphenol in xylene containing potassium carbonate with dimethyl sulphate offers an alternative to the classical route for musk ambrette. Hazards can be involved in this more well-known procedure consisting of the nitration of 6-tert-butyl-3-methylanisole (ref. 89) in acetic anhydride. 

If, however, 2-nitro-4-methylphenol is the result of ipso-attack para to the methoxy group there is no evidence for the change of the methoxy group substituent effect with acidity which was apparent with anisole itself. 

Din itro-6-methy I phenol 4,6-Di nitro-2-methylphenol. See 4,6-Dinitro-o-cresol... 

Amino-4-methylphenol 3-Amino-4-methylphenol 2-Amino-6-nitro-1-phenol-4-sulfonic acid 6-Amino-4-nitro-1-phenol-2-sulfonic acid m-Aminophenol... 

A series of twenty-nine substituted phenols (e.g., alkyl, phenyl, lluoro, diloro, bromo, nitro, and multisubstituted) was studied using a diol column and a 50/50 chloroform/iso-octane mobile phase [611]. In general, retention increased as the polar nature of the solute increased (e.g., in order of increasing retention 2,4,6-tributylphenol < 4-amylphenol < 4-methylphenol < phenol < 4-chlorophenol < 4-nitrophenol). As might be expected, this system showed good isomer selectivity (A for 3-nitrophenol = 4.20, for 4-nitrophenol = 5.50). However this selectivity was not as pronounced as that found using an underivatized silica support. 

Scheme 8.41. A representation of the formation of 2-nitro-4-methylphenol by the nitration of 4-methylphenol.

The phenoxy radical, derived from an H-abstraction reaction by NO, couples with another -NO molecule to give 4-nitrocyclohexa-2,5-dienone, which readily rearranges, after a keto-enol tautomerism to 2,6-di- -butyl-4-nitrophenol. 2,4-di-t-butylphenol and 4-r-butylphenol react in the same way, whereas the presence of three substituents on the aromatic ring of 2,4,6-tri-r-butylphenol and 2,6-di- butyl-4-methylphenol does not allow keto-enol tautomerism in these cases 2,4,6-tri- -butyl-4-nitrocyclohexa-2,5-dienone and 2,6-di-r-butyl-4-methylnitrocyclohexa-2,5-dienone were the sole nitro compounds obtained. The reaction between NO and 2,6-di-t-butylphenol or 2,4-di- -butylphenol in methanol resulted in phenoxyl radical dimerisation together with nitration. As shown in (Scheme 5.100), phenoxyl radical dimerises to give an... 

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