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Nitroaniline
The term nitroaniline in chemistry refers to a derivative of aniline (C6H5NH2) containing a nitro group (—NO2) There are three simple nitroanilines of formula C6H4(NH2)(NO2) which differ only in the position of the nitro group: * 2-Nitroaniline * 3-Nitroaniline * 4-Nitroaniline Some more complicated molecules with other substituent In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...s can also be referred to as nitroanilines, for example 4-chloro-3-nitro-aniline. {{Chemistry index Nitrobenzene derivatives ...
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4-Nitroaniline
4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor. Synthesis 4-Nitroaniline is produced industrially via the amination of 4-nitrochlorobenzene:] :ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl Below is a laboratory synthesis of 4-nitroaniline from aniline. The key step in this reaction sequence is an electrophilic aromatic substitution to install the nitro group ''para'' to the amino group. The amino group can be easily protonated and become a meta director. Therefore, a protection of the acetyl group is required. After this reaction, a separation must be performed to remove 2-nitroaniline, which is also formed in a small amount during the reaction. Applications 4-Nitroaniline is mainly consumed industrially as a prec ...
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2-Nitroaniline
2-Nitroaniline is an organic compound with the formula H2NC6H4NO2. It is a derivative of aniline, carrying a nitro functional group in position 2. It is mainly used as a precursor to o-phenylenediamine. Synthesis 2-Nitroaniline is prepared commercially by the reaction of 2-nitrochlorobenzene with ammonia: :ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl Many other methods exist for the synthesis of this compound. Direct nitration of aniline is inefficient since anilinium is produced instead. Nitration of acetanilide gives only traces of 2-nitro isomer is obtained due to the great steric effect of the amide. Sulfonation is usually used to block the 4 position and increases the effectiveness to 56%. Uses and reactions 2-Nitroaniline is the main precursor to phenylenediamines, which are converted to benzimidazoles, a family of heterocycles that are key components in pharmaceuticals. Aside from its reduction to phenylenediamine, 2-nitroaniline undergoes other reactions anticipated for a ...
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3-Nitroaniline
3-Nitroaniline is an organic compound with the formula H2NC6H4NO2. A yellow solid, it is a derivative of aniline, carrying a nitro functional group in position 3. It is an isomer of 2-nitroaniline and 4-nitroaniline. It is used as a precursor to dyes. Synthesis and applications 3-Nitroaniline is produced on a commercial scale by reduction of 1,3-dinitrobenzene with hydrogen sulfide, or sodium sulfide (a Zinin reaction). It is used as a chemical intermediate for azo coupling In organic chemistry, an azo coupling is an organic reaction, reaction between a diazonium compound () and another aromatic compound that produces an azo compound (). In this electrophilic aromatic substitution reaction, the aryldiazonium cation ... component and the dyes disperse yellow 5 and acid blue 29. References {{DEFAULTSORT:Nitroaniline, 3- Anilines Nitrobenzene derivatives ...
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Aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, aniline is "electron-rich". It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone to oxidation: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. Ani ...
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Nitro Group
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitro group is also strongly electron-withdrawing. Because of this property, bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid. Synthesis Preparation of aromatic nitro compounds Aromatic nitro compounds are typically synthesized by nitration. Nitration is achieved using a mixture of nitric acid and sulfuric acid, which produce the nitronium ion (), which is the electrophile: + The nitration product produced on the largest scale, by f ...
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Substituent
In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond replacing one hydrogen; ''-ylidene'' and ''-ylidyne'' are used with double bonds and triple bonds, respectively. In addition, when naming hydrocarbons that contain a substituent, positional numbers are used to indicate which carbon atom the substituent attaches to when such information is needed to distinguish between isomers. Substituents can be a combination of the inductive effect and the mesomeric effect. Such effects are also described as electron-rich and electron withdrawing. Additional steric effects result from the volume occupied by a substituent. The phrases ''most-substituted'' and ''least-substituted'' are frequently used to describe or compare molecules that are products of a chemical reaction. In this terminology, ...
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