Category: 14248-66-9

Safety of 3,5-Dimethyl-4-nitropyridine 1-oxide. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Nucleophilic displacements in substituted pyridine N-oxides. I. Kinetics of the reactions between sodium ethoxide and 2- and 4-bromo-, 4-chloro-, 2-, 3-, and 4-nitro-, 4-chloro-3,5-dimethyl-, and 3,5-dimethyl-4-nitropyridine 1-oxide in anhydrous ethanol. Author is Johnson, Ronald Mark.

Rates of reaction of halo and nitro pyridine N-oxides with sodium ethoxide in anhydrous ethanol were measured and the Arrhenius parameters calculated and discussed. The reaction rates, entropies, and energies of activation for nitro group displacements all decrease in the order 2 > 4 > 3. With the bromopyridine N-oxides both the entropy and energy of activation decrease in the order 4 > 2, but the positional reactivity is 2 > 4. Two methyl groups adjacent to the leaving group retard the reactions of 4-bromo-and 4-nitro-3,5-dimethylpyridine 1-oxide (I). Low activation energies are attributed to hindrance of nitro group conjugation in the ground state, either by N-oxide, oxygen dipolar repulsion (for 2-nitropyridine 1-oxide) or steric inhibition (in I). Small neg. or small pos. values obtained for activation entropies are attributed to extensive desolvation in forming the transition state. The very high entropy of activation for the reaction of 2-nitropyridine 1-oxide is attributed to the increased freedom of rotation of the nitro group in the transition state compared to the restriction imposed by the N-oxide oxygen in the ground state.

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Isoxazole – Wikipedia,
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Computed Properties of C7H8N2O3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Methyl-substituted 4-nitropyridine N-oxides as ligands: Structural, spectroscopic, magnetic and cytotoxic characteristics of copper(II) complexes. Author is Puszko, Aniela; Wasylina, Lucyna; Pelczynska, Marzena; Staszak, Zbigniew; Adach, Anna; Cieslak-Golonka, Maria; Kubiak, Maria.

Seven new mono- and dinuclear Cu(II) complexes containing various Me substituted 4-nitropyridine N-oxides as ligands were isolated and characterized physicochem. and biol. The characterization included elemental anal., magnetic and spectroscopic methods (diffuse reflectance and UV-visible absorption, IR, FIR). A single crystal x-ray diffraction anal. was performed for the complex with 2,5-dimethyl-4-nitropyridine N-oxide. Trans- and cis-square planar configuration around Cu ion was established for mono- and dinuclear species, resp. In methanolic solutions the dinuclear species decompose into mononuclear ones with increasing 4 → 6 coordination number with attachment of two solvent mols. The IR spectra showed that the strength of the Cu-ligand bond gauged by the degree of N-O elongation changed irregularly with position and number of Me groups. Cytotoxic studies on the MCF-7 human breast cancer line revealed a structure-activity relation: double blocking of the NO2 group with two CH3 groups rendered the complex completely inactive. The complexes were not significantly active against human cancer cell lines A549 (non-small cell lung carcinoma) and HL-60 (human promyelocytic leukemia) (no data).

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Electrophilic properties of nitroheterocyclic compounds..Name: 3,5-Dimethyl-4-nitropyridine 1-oxide.

Investigation of the reduction potential and calculation of the partition coefficient n-octanol/water allow the assessment of the potential suitability of nitropyridine N-oxide compounds in radiotherapy of cancer. Experiments were carried out using cyclic voltammetry with HMDE as working electrode. The electrode reduction of the investigated compounds is quite irreversible and strongly dependent on pH.

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Application In Synthesis of 3,5-Dimethyl-4-nitropyridine 1-oxide. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about The crystal and molecular structures of 3-methyl-4-nitropyridine N-oxide and 3,5-dimethyl-4-nitropyridine N-oxide. Author is Shiro, Motoo; Yamakawa, Masumi; Kubota, Tanekazu.

The crystal structures of 3-methyl-4-nitropyridine N-oxide (I), tetragonal 3,5-dimethyl-4-nitropyridine N-oxide (II) and orthorhombic 3,5-dimethyl-4-nitropyridine N-oxide (III) determined I is orthorhombic, space group P212121, with a 21.359(2), b 6.111(1), and c 5.132(1) Å; Z = 4. II is tetragonal, space group P41212, with a 7.443(1), and c 13.447(1) Å; Z = 4. III is orthorhombic, space group Pbca, with a 7.329(1), b 14.912(2), and c 13.852(2) Å; Z = 8. The intensity data were collected on a 4-circle diffractometer by use of Zr-filtered Mo Kα radiation. The structures were refined by a block-diagonal least-squares method to R = 0.062 for I (661 reflections), 0.051 for II (472) and 0.085 for III (941). The twist angles of the nitro group out of the mol. plane are 16.7, 49.4 and 51.1.degree., and the N-O distances of the N-oxide group are 1.292 (1.299 after libration corrections), 1.289 (1.293) and 1.302 (1.306) Å, resp. The contribution of the quinoid structure to the resonance forms is significant in the 2 mols., as in 4-nitropyridine N-oxide. The intramol. charge transfer from the N-oxide group O atom to the nitro group plays an important role in stabilizing these mols. in less-twisted conformations than those of their related compounds

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Derivatives of 4-amino- and 4-nitropyridine》. Authors are Essery, J. M.; Schofield, K..The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Quality Control of 3,5-Dimethyl-4-nitropyridine 1-oxide. Through the article, more information about this compound (cas:14248-66-9) is conveyed.

The following were prepared by conventional procedures. A series of substituted pyridine 1-oxides (substituent given): 3-Et (I), hygroscopic oil, b12 123-5°, picrate, m. 95°; 3-iso-Pr, b0.8 120-2°, picrate, m. 125-6°; 3-tert-Bu (Ia), b1 132-4°, picrate, m. 143-4°; 3,5-Me2, b0.1 116-18°, picrate, m. 135-6°; 2,3,5,6-Me4, needles, m. 139-40°, picrate, m. 144-5°; and 3-Br, -, picrate, m. 144.5-5.5°. I (24.5 g.), 65 ml. concentrated H2SO4 and 34 ml. concentrated HNO3 were warmed to 50° to initiate reaction, then heated 3.5 hrs. at 90-100°, the whole cooled, neutralized with solid K2CO3, filtered, the filtrate extracted with CHCl3 and the CHCl3 concentrated gave 19 g. 3-ethyl-4-nitropyridine 1-oxide (II), yellow needles, m. 68-9°. In similar fashion were prepared the following substd. 4-nitropyridine 1-oxides: 3-iso-Pr, m. 138-9°; 3,5-Me2 (IIa), m. 174-5° (picrate m. 137.5-8.5°); 2,3, 5,6-Me4 (IIb), m. 115-16° (picrate m. 160-1°); 3-Br, m. 156-7° [small amount of 3,4-Br(O2N)C5H3N also formed]. 3-tert-Butyl-2(or 6-)nitropyridine (IIc) m. 104.5-5.5°. To 5 g. II in 100 ml. dry CHCl3 at 0-10° was added 25 ml. PCl3, the whole kept 0.67 hr. at 10° poured on ice, treated with excess NaOH, extracted with CHCl3, and the CHCl3 extracts concentrated to give 3.8 g. 3,4-Et(O2N)C5H3N, b0.25 56-8°. Similarly were prepared 3,4-iso-Pr(O2N)C5H3N, b0.85 82-4° (picrate m. 106-7°); 3,5,4-Me2(O2N)C5H2N.0.5.H2O, m. 38-9° (picrate m. 169-70°); and 2,3,5,6,4-Me4(O2N)C5N.2H2O, m. 198-200° (picrate m. 174-6°). To 13 g. II was added 60 ml. AcCl; a vigorous reaction occurred. Subsequently, the mixture was poured on ice, the whole treated with excess NaOH and the product isolated via CHCl3 extraction to give 8.2 g. 4-chloro-3-ethylpyridine 1-oxide (IId), m. 86° (picrate m. 137-8°). The following substituted 4-chloropyridine 1-oxides were similarly prepared: 3-iso-Pr, hygroscopic, m. 87-8° (picrate m. 130-1°); 3,5-Me2 (III), m. 201-2° (picrate m. 142-3°); 2,3,5,6-Me4, m. 153-4° (picrate m. 154-5°); 3-Br, m. 153.5-4.5° (picrate m. 120-1°). III (2.5 g.) and 18 ml. concentrated aqueous NH3 heated 18 hrs. at 140°, the whole cooled, treated with 2.5 g. K2CO3, evaporated to dryness and the residue extracted with AcEt gave 1.6 g. 4-amino-3,5-dimethylpyridine 1-oxide-2H2O (IV), m. 227-9°, picrate m. 221-3°. 3,4-Me(O2N)C5H3N (2.5 g.), 50 ml. EtOH, 4 ml. 90% H2NNH2.H2O, and a small amount of Raney Ni (V) were heated 0.5 hr. on the steam bath, more V added, the whole filtered, and the filtrate concentrated to give 1.2 g. 3,4-Me(H2N)C5H3N, m. 108-9°. This procedure also gave 3,4-Et(H2N)C5H3N.0.5.H2O, m. 52-3° (picrate m. 196-7°); 3,4-iso-Pr(H2N)C5H3N.0.5.H2O, m. 69-70° (picrate m. 156-7°). To 0.5 g. IV in 5 ml. AcOH was added 0.3 g. Fe dust, the whole heated 1.5 hrs. on the steam bath, cooled, treated with excess NaOH and the product isolated via Et2O extraction to give 0.2 g. 3,5,4-Me2(H2N)C5H2N.2H2O (VI), m. 83-4° (picrate m. 226-7°). Alternately, 2 g. IIa, 25 ml. MeOH, 2 g. Raney Ni, and H gave 1.1 g. VI; the same procedure with IIb gave the amino derivative hemihydrate m. 196-7° (picrate m. 225-6°). Both reduction procedures with IIc gave the amino derivatives, m. 128-9°, λ 292, 228 mμ (log ε 3.56, 4.9) (picrate m. 242°). IId (3 g.) and 18 ml. 30% aqueous MeNH2 heated 18 hrs. at 140° gave, as above with IV, 2.1 g. 3-methyl-4-methylaminopyridine 1-oxide (VII), m. 106-7° (picrate m. 184-5°). Similarly were prepared the following substituted 4-methylaminopyridine 1-oxides: 3-Et, b0.5 120-2°, m. 117-18° (picrate m. 182-3°); 3-iso-Pr (VIII) (no m.p. given) (picrate m. 164-5°); 3,5-Me2, m. 94.5-5.5° (picrate m. 172-3°); 3-Br, hygroscopic solid (picrate m. 189-91°) and 2,3,5,6-Me4, hygroscopic solid (picrate m. 140-1°). VII reduced by Fe in AcOH gave 3,4-Me(MeNH)C5H3N, m. 125-6° (picrate m. 199-200°). VIII hydrogenated as above gave 3,3-iso-Pr-(MeNH)C5H3N, m. 95-6° (picrate m. 159-60°) and this procedure gave the following 3-substituted 4-(MeNH)C5H3N derivatives): 3,5-Me2, m. 119.5-20.5° (picrate m. 194.5-5.5°); 2,3,5,6-Me4, m. 118-19° (picrate m. 160-1°); 3-Br, 92-3°. The following were prepared by the above procedures: 3,4-Me(Me2N)C5H3N (IX), b1 73-5° (picrate m. 172-3°) and IX 1-oxide, b0.15 142-4° (picrate m. 130-1°); 3,4-Et(Me2N)C5H3N (X), b0.6 82-3° (picrate m. 118-19°) and X 1-oxide, b1 178-80° (picrate m. 139-40°); 3,4-iso-Pr-(Me2N)C5H3N (XI), b0.45 79-80° (picrate m. 138-9°) and XI 1-oxide, – (picrate m. 151-2°); 3,5,4-Me2(Me2N)C5H2N (XII), b0.4 69-7° (picrate m. 172-3°) and XII 1-oxide m. 83-4° (picrate m. 115-16°); and 3,4-Br(Me2N)C5H3N (XIII), b0.5 82-4° (picrate m. 182-3°) and XIII 1-oxide, – (picrate m. 160-1°). Ia (3.5 g.) and SO2Cl2 heated 2 hrs. at 110-20° gave 2 products, C9H12ClN, giving picrates, m. 152-3° and 149-50°.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Systematic coordination chemistry and cytotoxicity of copper(II) complexes with methyl substituted 4-nitropyridine N-oxides, published in 2011-08-31, which mentions a compound: 14248-66-9, mainly applied to preparation copper methylnitropyridine oxide; crystal structure copper methylnitropyridine oxide; antitumor activity copper methylnitropyridine oxide, Application In Synthesis of 3,5-Dimethyl-4-nitropyridine 1-oxide.

Three new nitrato Cu(II) complexes of di-Me substituted 4-nitropyridine N-oxide were synthesized and characterized by elemental anal., magnetic, spectroscopic, thermal and x-ray methods, resp. They were isolated as trans isomers, mononuclear (μ = 1.70-1.88 μB), five-(1-2) and four-(3) coordinate species [Cu(NO3)2(H2O)L2] where L = 2,3-dimethyl- or 2,5-dimethyl-4-nitropyridine N-oxide and [Cu(NO3)2L2], L = 3,5-dimethyl-4-nitropyridine N-oxide, resp. The x-ray crystal structure of (1) (L = 2,3-dimethyl-4-nitropyridine N-oxide) was determined The organic ligands, the complexes and copper hexaqua ion as a reference were tested in vitro on the cytotoxic activity against human cancer cell lines: MCF-7 (breast), SW-707 (colon) and P-388 (murine leukemia). The complexes are relatively strong cytotoxic agents towards P-388 cell line. Comparative anal. was performed for all known Cu(II) complexes containing Me derivatives of the 4-nitropyridine N-oxide from their composition, structure and cytotoxic activities. To obtain the typical structure for these species (i.e., 4-coordinate mononuclear trans-[Cu(inorganic anion)2L2]), two Me groups must be situated on both sides of N atom(s) (i.e., NO and NO2) in the ligand. The biol. activity is strongly dependent upon the number of the Me groups and the type of cell line. The best cytotoxic results were found for the complexes without substituents or with one Me group. Generally, for all cell lines, the complexation increased cytotoxicity when compared with the free ligands.

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Name: 3,5-Dimethyl-4-nitropyridine 1-oxide. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Studies on chemical carcinogens. XV. Carcinogenicity and mutagenicity of 4-nitropyridine 1-oxide derivatives. Author is Takahashi, Kazuhiko; Huang, Guang-Fu; Araki, Misako; Kawazoe, Yutaka.

The carcinogenicity and mutagenicity of 4-nitropyridine 1-oxide (I) [1124-33-0] and 7 of its alkyl derivatives were tested on mice and on Salmonella typhimurium strains and Escherichia coli strains. 3-Methyl compound [1074-98-2] was the most potent carcinogen, followed by 3-ethyl [35363-12-3] and then I. The mutagenicity was the most potent in 3-methyl derivative, 2,3-dimethyl [37699-43-7], and 2,5-Dimethyl [21816-42-2], moderate in I,and 2-Methyl [5470-66-6] and 2,6-dimethyl [4808-64-4], and to a least extent in 3,5-dimethyl [14248-66-9] derivative of I. Structure-mutagenicity relation was discussed on the basis of the mol. mechanism of the carcinogenesis of I. Quant. relation between mutagenicity and carcinogenicity was not strictly found among the compounds examined

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Formula: C7H8N2O3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Syntheses of sterically hindered zwitterionic pyridinium phenolates as model compounds in nonlinear optics. Part 2.. Author is Diemer, Vincent; Chaumeil, Helene; Defoin, Albert; Fort, Alain; Boeglin, Alex; Carre, Christiane.

Pyridinium phenolates possess a dissym. delocalized π-electron system providing a huge quadratic nonlinearity. They are a promising class of mols. for applications in photoelectronics and photonics. Semiempirical calculations indicate that the interplanar angle between the two aromatic rings leads to enhancement in the NLO properties of these compounds The confirmation of this feature may be provided by the study of a new series of sterically hindered pyridinium phenolates bearing two tert-Bu substituents at the ortho position(s) of the phenolate functionality. Such bulky groups would enhance the solubility of zwitterions in organic solvents and would limit the formation of aggregates. Their efficient preparations by using Suzuki cross-coupling reactions involving 3,5-dialkylated 4-bromopyridine N-oxides are described.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Berdys, Joanna; Makowski, Mariusz; Makowska, Monika; Puszko, Aniela; Chmurzynski, Lech researched the compound: 3,5-Dimethyl-4-nitropyridine 1-oxide( cas:14248-66-9 ).Electric Literature of C7H8N2O3.They published the article 《Experimental and Theoretical Studies of Acid-Base Equilibria of Substituted 4-Nitropyridine N-Oxides》 about this compound( cas:14248-66-9 ) in Journal of Physical Chemistry A. Keywords: nitropyridine oxide derivative acid base equilibrium acetonitrile thermodn. We’ll tell you more about this compound (cas:14248-66-9).

By using the potentiometric titration method, acidity constants in the polar aprotic solvent acetonitrile (in the form of pKaAN values) of cations obtained by protonation of 13 substituted 4-nitropyridine N-oxides and cationic homoconjugation constants (KBHB+) of the cationic acids conjugated with the N-oxides studied have been determined A correlation has been established between the tendency toward cationic homoconjugation (expressed as log KBHB+) and the basicity of the N-oxides in acetonitrile (pKaAN). Further, by using ab initio methods at the RHF and MP2 levels utilizing the Gaussian 6-31G* basis set, energies and Gibbs free energies have been determined of protonation and formation of homocomplexed cations stabilized by O···H···O bridges in the gas phase. The calculated protonation energies, ΔEprot, and Gibbs free enthalpies, ΔGprot, in vacuo have been found to correlate well with the acid dissociation constants (expressed as pKaAN values) of protonated N-oxides, whereas the calculated energies, ΔEBHB+, and Gibbs free energies, ΔGBHB+, of homoconjugation do not correlate with the cationic homoconjugation constant values determined in acetonitrile.

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Isoxazole – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzoylacetamide and iminobenzoylacetamide》. Authors are Checchi, Silvio; Papini, Piero.The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Related Products of 14248-66-9. Through the article, more information about this compound (cas:14248-66-9) is conveyed.

cf. CA 53, 21974b. BzCH2CN (I) was prepared in excellent yields from BzCH2CONH2 (II) and POCl3. Similar treatment of PhC(:NH)CH2CN (III) gave 6,3,2,4-Cl(CN)Ph2C5HN (IV), converted to give various 3,6-disubstituted 2,4-diphenylpyridines, N:CPh:CR:CPh.CH:CR’ (V). II (10 g.) and 18 g. POCl3 heated (H2O-free atm.) 30 min. on a steam bath at 60-70°, the cooled mixture decomposed with cold H2O, and the solid isolated and recrystallized repeatedly from H2O gave crystalline I, m. 70-2°. III (5 g.) and 8 g. POCl3 similarly heated 1 hr. at 70-80°, the cooled mass taken up in cold H2O, the washed (H2O, alc., Et2O) and dried product taken up in alc. containing a trace of HCl, and the crystalline material recrystallized from alc. yielded IV, m. 178-80°. IV (2 g.) refluxed 1 hr. in alc. containing 1 g. KOH and concentrated, the solution neutralized with dilute HCl, and the precipitate recrystallized from alc. gave V (R = CN, R’ = OH), m. 150°. IV (2 g.) heated 4 hrs. at 180° in a sealed tube with excess alc. NH3, the cooled mixture evaporated, and the product separated and recrystallized from ClCH:CCl2 yielded V (R = CN, R’ = NH2) hemihydrate, m. 214-15°. IV (5 g.) refluxed in alc. with powd. Zn, the filtered solution evaporated on a steam bath, and the residue taken up in a min. of HCONMe2 and diluted with H2O gave V(R = CN, R’ = H) (VI), m. 175-7° (alc.). VI (3 g.) heated 6 hrs. at 180-200° with concentrated HCl in a sealed tube, the liquid poured into hot H2O, the filtered solution neutralized with NH4OH, and the precipitate crystallized from alc. gave V(R = CO2H, R’ = H), m. 248-50°, decarboxylated by heating at 250° to V (R = R’ = H), characterized as the sulfate, m. 245° (darkening), and as the picrate, m. 187° (decomposition). IV (3 g.) refluxed 7 hrs. in 40% alc. KOH, the solvent evaporated, and the residue taken up in H2O and acidified with dilute HCl gave V (R = CONH2, R’ = OH), m. 287-9° (alc.), converted by heating 6 hrs. in a sealed tube at 180-90° with concentrated HCl to give V (R = H, R’ = OH), m. 210° (alc.) (also obtained similarly from IV); picrate m. 193-5° (alc.). VI (1 g.) boiled 2-3 min. in 4 ml. dilute H2SO4, the mixture boiled with addition of H2O, the cooled filtered solution made alk. with dilute NH4OH, and the precipitate crystallized from AcOEt and CHCl3 gave V (R = CONH2, R’ = H), m. 225-7°.

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Isoxazole – Wikipedia,
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