2-Methyl-4-nitrosophenol

Solid sodium nitrite (35 g., 0.51 mole) is added to a stirred suspension of 27 g. (0.25 mole) of o-cresol in 2 1. of ice-water slurry. A solution of 9.5 ml. of concentrated sulfuric acid in 200 ml. of water is added over a 1-hour period, the temperature being held below 5° by the further addition of ice. The mixture is allowed to stand for 2 hours, and the nitroso compound is filtered off and washed with water. Recrystallization of a small amount of the product from benzene gives pure 2-methyl-4-nitrosophenol, m.p. 136°. 

C7H7NO2, 2-Methyl-4-nitrosophenol.. 203 C7H7NO3, 2-Methyl-4-nitrophenol. 203... 

OMe, Cl, p-NH2, NHCH3, NMe2, N(Alkyl), NPh2 or Nitrosonaphtol, 2-methyl 4-nitrosophenol, Me-nitrosophenol... 

It can act either as a nitrosophenol or as a quinone monoxime. Coloured derivatives, e.g. the sodium salt, are derived from the quinone form. Direct methylation gives a coloured compound which has been shown to be quino-nemethoxime OlCeH4tNOCH3 p-nitrosoani-sole CH30 C6H4 N0 has been obtained by another route and is colourless. 

We note that the difference between the enthalpy of formation of the unsubstituted benzoquinone/nitrosophenol and that of its isopropyl methyl cymene-like disubstituted derivative is 146 kJmol, comparable to that of the corresponding hydrocarbons, benzene and its substituted counterpart as liquids, 127.0 1.2 kJmol, and as the corresponding phenols as solids, 144.4 9.6 kJmol . ... 

In Table 7, data for the B- and K-bands of o-hydroxybenzaldehyde and o-nitrosophenol, for the R-bands of the latter substance and of o-hydroxythiobenzophenone, and for the corresponding bands of them methyl ethers in hexane (or benzene) solution are shown. 

From diazotized aniline and p-nitrosophenol Borsche 88 obtained 2-hy-droxy-5-nitrosobiphenyl (XXIII) in 8% yield, and with 2-methyl-4-ni-trosophenol he obtained 2-hydroxy-3-methyl-5-nitrosobiphenyl (XXIV). 

Nitration of p-cymene by fuming nitric add leads to 2,4-dinitrotoluene.1184 Heating 1,6-dihydro-l-methyl-6-oxonicotinic acid with nitric acid (d 1.52) under reflux gives 1-methyl-3,5-dinitro-2(li/)-pyridone in good yield.1185 2,6-Dibromo-4-nitrosophenol is formed quantitatively from 3,5-dibromo-4-hydroxybenzoic acid and sodium nitrite in aqueous alcohol.166,1183 Nitrous acid replaces hydroxymethyl groups in phenols by nitro groups,1186 and diazonium salts replace them by diazo groups.1187... 

When furnace and thermal blacks are used, in contrast to the now rarely used channel blacks, it is necessary to employ a promoter. These promoters are usually nitroso compounds such as p-dinitroso-benzene (I), p-nitrosophenol (II), N-nitroso-N-methyl-p-nitrosoaniline (III) and N-(2-methyl-2-nitropropyl)-4-nitrosoaniline (IV) ... 

C7H7NO3, 5-Methoxy-2-nitrosophenol (red form), 23, 658 CBH7CIN2O3, 0-Methyl-p-nitrobenzohydroximoyl chloride, 43B, 89 CBH7NO2, 2-Hydroximino-1-phenylethan-1-one, 44B, 56 CBHBBrNO, anti-a-Bromoacetophenone oxime, 39B, 42 CBH1BN2O2, Nitrosoisobutane trans-dimer, 26, 608... 

Methyl-2-nitrosophenol, M-00207 (4-Methyl-5-nitro-2-thiazolyl)thiourea,... 

Diethylamino)-2-[(5-methyl-2-pyridinyl) azojphenol, D-00324 5-(Diethylamino)-2-nitrosophenol, in A-00285... 

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