Ortho-nitrotoluene
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Ortho-nitrotoluene
2-Nitrotoluene or ''ortho''-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes. Synthesis and reactions It is made by nitrating toluene at above -10 °C. This reaction affords a 2:1 mixture of 2-nitro and 4-nitro isomers. Chlorination of 2-nitrotoluene gives two isomers of the chloronitrotoluenes. Similarly nitration gives two isomers of dinitrotoluene. 2-Nitrotoluene is mainly consumed in the production of o-toluidine ''o''-Toluidine (''ortho''-toluidine) is an organic compound with the chemical formula CH3C6H4NH2. It is the most important of the three isomeric toluidines. It is a colorless liquid although commercial samples are often yellowish. It is a precu ..., a precursor to dyes. References External linksCDC - NIOSH Pocket Guide to Chemical Ha ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ...
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Nitration
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol (chemistry), alcohols and nitric acid (as occurs in the Organic synthesis, synthesis of nitroglycerin). The difference between the resulting molecular structures of nitro compounds and nitrates () is that the nitrogen atom in nitro compounds is directly Chemical bond, bonded to a non-oxygen atom (typically carbon or another nitrogen atom), whereas in nitrate esters (also called organic nitrates), the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom (nitrito group). There are many major industrial applications of nitration in the strict sense; the most important by volume are for the production of nitroaromatic compounds such as nitrobenzene. The technology is long-standing and mature. : Nitration rea ...
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Toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC nomenclature of organic chemistry, IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent. As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant and has the potential of causin ...
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O-toluidine
''o''-Toluidine (''ortho''-toluidine) is an organic compound with the chemical formula CH3C6H4NH2. It is the most important of the three isomeric toluidines. It is a colorless liquid although commercial samples are often yellowish. It is a precursor to the herbicides metolachlor and acetochlor. Synthesis and reactions ''o''-Toluidine is produced industrially by nitration of toluene to give a mixture of nitrotoluenes, favoring the ortho isomer. This mixture is separated by distillation. 2-Nitrotoluene is hydrogenated to give o-toluidine. The conversion of ''o''-toluidine to the diazonium salt gives access to the 2-bromo, 2-cyano-, and 2-Chlorotoluene, 2-chlorotoluene derivatives. N-acetylation is also demonstrated. Safety The LD50 (oral, rats) is 670 mg/kg. Binding of hemoglobin ''o''-Nitrosotoluene, a metabolite of ''o''-toluidine, converts hemoglobin to methemoglobin, resulting in methemoglobinemia. ''o''-Nitrosotoluene is suspected of causing bladder cancer in rats. Nitro ...
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Nitrotoluenes
Mononitrotoluene or nitrotoluene (MNT or NT), is any of three organic compounds with the formula C6H4(CH3)(NO2). They can be viewed as nitro derivatives of toluene or as methylated derivatives of nitrobenzene. Mononitrotoluene comes in four isomers, differing by the relative position of the methyl and nitro groups. All are pale yellow with faint fragrances: * ''ortho''-nitrotoluene (also called ONT, ''o''-nitrotoluene, or 2-nitrotoluene). m.p. = −10.4 °C * ''meta''-nitrotoluene (MNT, ''m''-nitrotoluene, or 3-nitrotoluene). m.p. = 16 °C * ''para''-nitrotoluene (PNT, ''p''-nitrotoluene, or 4-nitrotoluene). m.p. = 44.5 °C * , in which the benzylic carbon is nitrated. m.p. = 80.7 °C. Typical use of nitrotoluene is in production of pigments, antioxidants, agricultural chemicals, and photographic chemicals. ''Ortho''-mononitrotoluene and ''para''-mononitrotoluene can be also used as detection taggants for explosive detection. See also * Toluene * D ...
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