Cresols, nitro

Picric acid Dinitro- phenol TNT Trinitro- cresol Nitro- naphtha- lene Dinitro- naphtha- lene... 

Nitromersol/777-j5 , y (4) and mercurophen [52486-78-9] (5) are prepared by the same mercuration reaction as phenyhnercuric acetate, only 4-nitro-(9-cresol and o-nitrophenol are used, respectively, iastead of benzene. The second step is reaction with sodium hydroxide to form the anhydride or sodium salt, respectively. 

Musk ambrette, which is usually regarded as the finest of all the artificial musks, is a nitro-compound of the methyl ether of butyl-meta-cresol, usually described as dinitro-butyl- ieia-cresol methyl ether. It should melt at 85°. 

Mononitro Methyl Anisole (2-Nitro-4-methyl anisole, 3-Nitro4-methoxy l-methyl benzol or Methyl- [2-nitro4 methyl phenyl]-ether). CH3.0.(N02)C6H3.CH3, mw 167.18, N 8.38%, OB to C02-167.48%, pale yellow cryst, mp 8.5°, bp 274° (partial decompn), d 1.2025 g/cc at 25/4°, Rl 1.5536 si sol in eth (Ref 1). Prepd by heating K2-nitro-p-cresol with methyl-iodide methylalc in a sealed tube at 100°... 

In mononitration the hazard is due to the extremely violent reaction of the unreacted hydrocarbon with the MA, and to the fact that nitro derivatives of cresols are formed in the process, along with nitro toluenes. The last stage — trinitration — is dangerous due to the drastic conditions of the reaction which requires coned acids and a high temp. The earlier method of trinitration at which temps up to 120° were applied was particularly hazardous. If the mono-nitre toluene hns not b n freed from nitro-cresols, trinitration is still more dangerous, due to the high reactivity of nitrocresols, and their liability to undergo oxidation... 

Nitro-4-cresol was to be manufactured by adding 4-toluidine to nitric acid. One carboy of nitric acid was charged into the reactor, but the next one charged actually contained oleoyl chloride in error. The violent reaction ensuing ruptured the reactor and there was a fire. 

Chemical/Physical. Products identified from the reaction of toluene with nitric oxide and OH radicals include benzaldehyde, benzyl alcohol, 3-nitrotoluene, p-methylbenzoquinone, and o, m, and p-cresol (Kenley et ah, 1978). Gaseous toluene reacted with nitrate radicals in purified air forming the following products benzaldehyde, benzyl alcohol, benzyl nitrate, and 2-, 3-, and 4-nitro-toluene (Chiodini et al., 1993). Under atmospheric conditions, the gas-phase reaction with OH radicals and nitrogen oxides resulted in the formation of benzaldehyde, benzyl nitrate, 3-nitrotoluene, and o-, m-, and p-cresol (Finlayson-Pitts and Pitts, 1986 Atkinson, 1990). 

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). 

Ethyl-(4 nitro-3-methylpbenyl)-etber, C6H3(CH3)(N02)0C2H5 mw 181.18, N7.73% prisms (pet eth), mp 55°. Prepd from ethyl iodide in eth and the silver salt of 6-nitro m-cresol... 

Problem 19.3 Write structural formulas for (a) p-cresol, (b) 2-nitro-4-bromophenol, (c) 4- -hexylresorcinol, (d) ethyl salicylate, (e) /3-naphthol. 

Problem 19,14 Assign numbers from 1 for least to 4 for most to indicate the relative acid strengths in the following groups (a) phenol, m-chlorophenol, m-nitrophenol, m-cresol (b) phenol, benzoic acid, p-nitro-phenol, carbonic acid (c) phenol, p-chlorophenol, p-nitrophenol, p-cresol (d) phenol, o-nitrophenol, m-nitrophenol, p-nitrophenol (e) phenol, p-chlorophenol, 2,4,6-trichlorophenol, 2,4-dichlorophenol (/) phenol, benzyl alcohol, benzenesulfonic acid, benzoic acid. ... 

A method for theroutine estimation of 3, 5"3i nitro-o-cresol in urine is reported by Parker (Ref 12)... 

Dinitro-p-cresol, yel-brn ndls (from ale), mp 112-13° prepd by nitrating 2-nitro-p-cresol in AcOH at 18-25°with HN03, together with other products (Ref 3, p [ 391 ] )... 

Tetrani trocresol (TeNCrs). Only one isomer is known 2,4,5,6 Tetranitro-m-cresol, CH3.Cg(N02)4.0H mw 288.13, N 19.45% col crysts (from chlf) having a bitter taste, mp 175°, bp explodes readily sol in ale or w, giving yel solns was prepd by nitrating 5-nitro-m-cresol with coned HN03 coned H2S04 at 50°. This compd is a powerful expl (Refs 1 2) Refs 1) Beil 6, 388 2) J.J. Blanksma, Rec 27,... 

Compounds from o-Nitro-p-cresol and 2 6-Dinitrophenol.—These phenols yield respectively (C6H5)4Cr.0.C6H3(N02)CH3, red needles, M.pt. 135° C. with explosion, and (C6H5)4Cr.0.C6H3(N02)2, orange-red plates, melting and violently exploding at 160° C. 

It is convenient to have a method for the detection and rough estimation of urease activity in gels. A simple staining procedure using cresol red has been described (27), but a more elaborate procedure (28) employing p-nitro blue tetrazolium results in sharper definition. 

J- and y-TNT lose their active nitro group by the action of aqueous alkali and yield salts of dinitro-m-cresol.29 The mixed dinitro-m-cresols which result may be nitrated to trinitro-m-cresol, a valuable explosive. Their salts, like the picrates, are primary explosives and sources of danger. - and y-TNT react with lead oxide in alcohol to form lead dinitrocresolates, while a-TNT under the same conditions remains unaffected. 

The addition of mercuric nitrate is here written as a 1,4-addition, but 1,2-addition would give the same final product, and there is no evidence in the facts concerning benzene which enables us to choose between the alternative hypotheses. Toluene yields tri-nitro-m-cresol by a similar series of reactions, and it is clear that the nitro group in the addition product of mercuric nitrate and toluene has taken either the 2-, the 4-, or the 6-position, that is, one or the other of the positions activated by the methyl group. In the addition of mercuric nitrate to naphthalene, the nitro group correspondingly may be supposed to go to the active a-position. If the addition is 1,2-, the product on oxidation will yield a derivative of /J-naphthol. If it is 1,4-, it will yield a derivative of a-naphthol. The two possibilities are indicated below. 

N 3.38% pale red plates mp, darkens at 220° and explds violently at 228°. Sol in chlf, carbon tetrachloride toluene insol in It petr. Prepn is by reacting an aq soln of Tl diethyl hydroxide with 4-nitro-m-cresol Ref A. Goddard, JCS 119,1310-15 (1921) CA 15,3635 (1921)... 

The Dinitro Methoxy Toluenes. See in Vol 3, C556-R to C557-L under Nitro Derivatives of Cresol . The CA Registry No for these compds is [50741-92-9]... 

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