14452-34-7Relevant articles and documents
Nitration of phenolic compounds by antimony nitrate
Jirandehi, Hassan Fathinejad,Mirzaeian, Marjan
, p. 284 - 286 (2011)
Antimony nitrate is new compound to be an efficient nitration reagent in the nitration of phenolic compounds with high yields. This producerworks efficiently onmost of the examples, as a grinding nitration reaction, proceed very fast (~1 min) and thermogenic. Copyright Taylor & Francis Group, LLC.
Improved Protocol for Mononitration of Phenols with Bismuth(III) and Iron(III) Nitrates
W?sińska, Ma?gorzata,Korczewska, Anna,Giurg, Miros?aw,Skarzewski, Jacek
supporting information, p. 143 - 150 (2015/10/20)
A simple and efficient multigram procedure was developed for the selective mononitration of various activated phenols. The reaction proceeded smoothly with 0.5 equivalents of Bi(NO3)3 · 5H2O or Fe(NO3)3 · 9H2O in acetone at ambient temperature or at reflux. The desired products were isolated in 62-93% total yield and essentially no overnitrated compounds were detected.
Synthesis of new carbon-11 labeled benzoxazole derivatives for PET imaging of 5-HT3 receptor
Gao, Mingzhang,Wang, Min,Hutchins, Gary D.,Zheng, Qi-Huang
, p. 1570 - 1574 (2008/09/21)
5-HT3 receptor is an attractive target for the development of therapeutic agents for use in brain, heart and cancer diseases, and imaging agents for use in biomedical imaging technique PET. Benzoxazole derivatives are a novel class of 5-HT3 receptor partial agonists with high binding affinity. Carbon-11 labeled benzoxazole derivatives have been synthesized as new potential PET radioligands for imaging 5-HT3 receptor. The target tracers were prepared by N-[11C]methylation of their corresponding precursors using [11C]CH3OTf and isolated by HPLC purification procedure in 40-50% radiochemical yields, which were decay corrected to the end of bombardment (EOB), based on [11C]CO2. The overall synthesis time was 20-25 min from EOB. The radiochemical purity was >99%, and specific activity was in a range of 74-111 GBq/μmol at the end of synthesis (EOS).
Photochemical nitration by tetranitromethane. Part XXXVII. Adduct formation and the regiochemistry of attack of trinitromethanide ion on radical cations in the photochemical reactions of 2-methyl-, 2,3-dimethyl- and 2,4-Dimethylanisoles
Butts, Craig P.,Eberson, Lennart,Hartshorn, Michael P.,Robinson, Ward T.,Timmerman-Vaughan, David J.
, p. 73 - 87 (2007/10/03)
The photolysis of the charge transfer (CT) complex of tetranitromethane and 2-methylanisole 2 in dichloromethane at 20 °C gives the epimeric 1-methoxy-6-methyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 8 and 9 in addition to 2-methyl-4-trinitromethylanisole (3) and 2-methyl-4-nitroanisole (4). In acetonitrile the yields of compound 4 and adducts 8 and 9 are significantly higher. Similar reaction of 2,3-dimethylanisole (6) in dichloromethane gave nitro-trinitromethyl adducts 10 and 11, hydroxy-trinitromethyl adducts 12 and 13, 2,3-dimethyl-5-trinitromethylanisole (14), 4-methoxy-2,3-dimethylbenzonitrile N-oxide (15), 2,3-dimethyl-4-trinitromethylanisole (16), 2,3-dimethyl-4-nitroanisole (17), 2,3-dimethyl-4,6-dinitrophenol (18), 3-methoxy-4,5-dimethyl-benzoic acid (19) and the hydroxy dinitro compound (20). The photolysis of the CT complex of 2,4-dimethylanisole (7) with tetranitromethane in dichloromethane gave the epimeric 1-methoxy-4,6-dimethyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 21 and 22, together with 4,6-dimethyl-3-trinitromethylanisole (23), 4,6-dimethyl-2-nitrophenol (24), 4,6-dimethyl-2-trinitromethylanisole (25), 4,6-dimethyl-3-nitroanisole (26), 4,6-dimethyl-2-nitroanisole (27) and 4,6-dimethyl-4-nitrocyclohexa-2,5-dienone (28). The modes of formation of the above products are discussed, including the effects of the reaction solvent on those processes. The X-ray crystal structure of 1-methoxy-2-methyl-c-6-nitro-r-3-trinitromethylcyclohexa-1,4-diene (9) is reported. Acta Chemica Scandinavica 1997.
15N Nuclear Polarisation in Nitration and Related Reactions. Part 7. The Mechanisms of Rearrangement of 4-Methyl-4-nitrocyclohexa-2,5-dienones
Ridd, John H.,Trevellick, Susan,Sandall, John P. B.
, p. 1535 - 1540 (2007/10/02)
The rearrangement of 4-methyl-4-nitrocyclohexa-2,5-dienone to 4-methyl-2-nitrophenol has been studied in acetic anhydride at 22-37.5 deg C in the presence of varying concentrations of sulfuric acid.Similar studies have been carried out on the 15N labelled compound and on the effects of some substituents (2-Me, 3-Me, 2-NO2).During reaction, the thermal rearrangement of the labelled compound gives very strongly enhanced 15N NMR absorption signals (enhancement coefficient ca. 1000) for both the substrate and the product.For acid catalysed reaction, the enhancement coefficient of the signals is less (ca. 130) but still sufficient to indicate a homolytic reaction path.This interpretation is shown to be consistent with the properties of the radicals involved and with the substituent effects observed.
Tobacco smoke chemistry. 2. Alkyl and alkenyl substituted guaiacols found in cigarette smoke condensate.
Arnarp,Bielawski,Dahlin,Dahlman,Enzell,Pettersson
, p. 44 - 50 (2007/10/02)
A series of alkyl and alkenyl substituted guaiacols, which comprise a group of biologically and organoleptically active compounds, have been synthesized. Mass spectra and GC retention times for these have been recorded and compared with those obtained for constituents of a weakly acidic fraction of smoke condensate derived from American blend type cigarettes. On the basis of these results, 25 guaiacols have been identified, 18 of which have not been detected in tobacco smoke condensate previously.
FORMATION OF DIENONES ON THE REACTION OF CRESOLS, XYLENOLS, AND 2-NAPHTHOL WITH NITROGEN DIOXIDE: OBSERVATION OF KETO TAUTOMERS OF NITROPHENOLS
Fischer, Alfred,Mathivanan, N.
, p. 1869 - 1872 (2007/10/02)
Reaction of o- and p-cresol, the xylenols, and 2-naphthol with nitrogen dioxide gives nitrocyclohexadienones and nitrophenols.Secondary nitrodienones, the keto tautomers of the nitrophenols, have been observed in several cases and are intermediates in the formation of the nitrophenols.
ipso Nitration. XXIV. Nitration of 2-methylphenols. Formation and rearrangement of 6-methyl-6-nitrocyclohexa-2,4-dienones
Cross, Gordon G.,Fischer, Alfred,Henderson, George N.,Smyth, Trevor A.
, p. 1446 - 1451 (2007/10/02)
Nitration of o-cresol and some mono-, di-, and trimethyl derivatives in acetic anhydride at -60 deg C gives 6-methyl-6-nitrocyclohexa-2,4-dienones.The dienones are more labile than the isomeric 4-methyl-4-nitrocyclohexa-2,5-dienones and, if the 2-position of the dienone is not blocked, undergo regiospecific rearrangement to 6-nitro-o-cresols. 2,3,6-Trimethyl- and 2,3,5,6-tetramethylphenol also give a 2,5-dienone with nitro attached to a secondary carbon.