619-15-8Relevant articles and documents
Synthesis method of 2-methyl-4-nitrobenzoic acid
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Paragraph 0010, (2017/01/02)
The invention discloses a synthesis method of 2-methyl-4-nitrobenzoic acid, and belongs to the technical field of chemosynthesis. According to the method, methylbenzene is used as raw materials; reaction liquid formed by mixing concentrated nitric acid and concentrated sulfuric acid is added for mixing; after being washed by a sodium hydroxide solution, the materials take an reaction with stannous chloride, iron powder and glacial acetic acid; then, hydrochloric acid is dropwise added for mixing to obtain 2-amino-5-nitrotoluene; then, the 2-amino-5-nitrotoluene is mixed with acetic acid and the concentrated sulfuric acid for taking a reaction; after the oxidization by an oxidizing agent of sodium perborate, temperature lowering by ice water and washing by deionized water are carried out; then, under the oxidization effect of an oxidizing agent of potassium permanganate, the materials are mixed with hydrochloric acid for reaction; then, still standing, suction filtering and drying are carried out, and the 2-methyl-4-nitrobenzoic acid is obtained. The synthesis method has the beneficial effects that the synthesis process is simple; the cost is low; byproducts are few; the yield of obtained products is as high as more than 95 percent; the purity is as high as more than 99 percent.
An "ortho effect" in electrophilic aromatic nitrations: Theoretical analysis and experimental validation
Li, Hui-Jing,Wu, Yan-Chao,Dai, Jian-Hong,Song, Yan,Cheng, Runjiao,Qiao, Yuanyuan
, p. 1307 - 1312 (2015/02/05)
Usually, a π-donor substituent acts as an ortho/para directing group in an electrophilic aromatic substitution reaction, and a π-acceptor substituent acts as a meta directing group. Interestingly, when a π-acceptor substituent is meta to a π-donor substituent, certain electrophilic aromatic nitration occurs ortho to the π-acceptor substituent rather than para . The "ortho effect", highlighted in various textbooks, has been tentatively analyzed here based on ab initio calculations. The reliability of the calculations was verified by the corresponding experimental data, including a newly-designed electrophilic aromatic nitration that also gave reasonable product distributions.
Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: A photoelectron spectroscopy and ab initio investigation
Rondino, Flaminia,Catone, Daniele,Mattioli, Giuseppe,Bonapasta, Aldo Amore,Bolognesi, Paola,Casavola, Anna Rita,Coreno, Marcello,O'Keeffe, Patrick,Avaldi, Lorenzo
, p. 5272 - 5282 (2014/01/23)
We present an investigation of the close relationship between chemical structure, physical properties and reactivity of the three nitrotoluene isomers: a joint experimental and theoretical study, based on X-ray photoelectron spectroscopy (XPS) measurements and ab initio calculations, addressing the complex interplay between the competing electron-donor and electron-acceptor effects of the nitro- and methyl-substituents on the chemical properties of the nitrotoluene isomers. As the main results of the investigation we: (i) point out that accurate ab initio calculations play a key role in the complete assignment of photoemission measurements, as well as in the estimate of proton affinities in the case of all the eligible sites; (ii) revisit, at a more quantitative level, textbook models based on inductive and resonant effects of different substituents of the aromatic ring, as well as on the hyper-conjugative connection of the methyl group to the π-conjugated system; (iii) provide an accurate analysis of correlation patterns between calculated proton affinities and core-ionization energies, which represent a powerful tool, capable of predicting site-specific reactivities of polysubstituted molecules in the case of electrophilic aromatic substitution reactions.
DIHYDROBENZOFURAN DERIVATIVES AS INSECTICIDAL COMPOUNDS
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Page/Page column 93; 94, (2014/09/29)
Provided are compounds of formula (I) and methods of controlling insects, acarines, nematodes or molluscs, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I).
PROCESS FOR THE PREPARATION OF NITRATED AROMATICS AND MIXTURES THEREOF
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Page/Page column 4, (2012/01/03)
A process for the preparation of mononitroaromatics and dinitroaromatics, in which a hydrate melt of at least one metal nitrate M(NO3)3 is used as a nitrating medium, it being possible for M to be the metals Fe, Cr, Y, La, Ce, Al, Bi and In, and the metal nitrate having a water content of from 4 to 9 mol of water per M(NO3)3, leads to simplifications of the process and improved yields.
Zirconium-catalysed Oxidation of Primary Aromatic Amines to Nitro Compounds Using tert-Butylhydroperoxide
Krohn, Karsten,Kuepke, Jochen,Rieger, Hagen
, p. 335 - 339 (2007/10/03)
A broad range of primary aromatic amines (1a-x) with electron donating and accepting substituents are oxidized in good to excellent yields to the nitro compounds 3a-x using tert-butylhydroperoxide as the oxidant and Zr(OtBu)4 as the catalyst. The corresponding nitroso compounds 2m,-2n, 2s and 2u can be isolated in the conversion of electron-rich anilines 1m, 1n, 1s and 1u. The aminopyridines 5a-d are also converted to the corresponding nitropyridines 6a-d, but in lower yields (41-47%).
Addition and Redox Processes in the Reaction of Grignard Reagents with 1,4-Dinitrobenzene. Factors affecting Produdct Distribution
Bartoli, Giuseppe,Dalpozzo, Renato,Grossi, Loris
, p. 573 - 578 (2007/10/02)
1,4-Dinitrobenzene (1) reacts smootly and irreversibly with alkyl-magnesium or -lithium reagents to give at first the nitroarene radical anion (3) (redox product) and 6-alkyl-2-nitro-5-aci-nitrocyclohexa-1,2-diene (4) (addition product).Intermediate (4) undergoes an immediate addition to the nitro function by a second mole of RMgX or RLi to give trans-4,5-dialkyl-3,6-di-aci-nitrocyclohexene (5), which can be converted into the corresponding trans-5,6-dialkyl-1,4-dinitrocyclohexa-1,3-diene (6) by oxidation with sodium hypochlorite or dichlorodicyanobenzoquinone.The addition process is favoured by lower temperatures and weakly polar and highly viscous solvents, while steric hindrance in the magnesium reagent enhances radical anion (3) formation.These findings are interpreted in terms of a single electron-transfer mechanism in which all factors delaying a geminate recombination of the radical pair favour the redox process to the detriment of addition.The almost absolute stereoselectivity of the double alkylation process is attributed to steric control on the direction of attack of RM to the ene-nitro function of (4) exerted by the axial alkyl group.A detailed e. s. r. study of 1,4-dinitrobenzene radical anion is also reported.
Process for the production of nitro derivatives of aromatic compounds
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, (2008/06/13)
Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.
