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1-chloro-2,4-dinitrobenzene → 1-fluoro-2,4-dinitrobenzene 5-chloro-2-nitrobenzotrifluoride → 5-fluoro-2-nitrobenzotrifluoride 1,3-dichloro-4-nitrobenzene → 1,3-difluoro-4-nitrobenzene 2,6-dichlorobenzonitrile → 2,6-difluorobenzonitrile. The nitro groups in the above compounds can be reduced to give the corresponding aniline. For example ...
4-Fluoroaniline is an organofluorine compound with the formula FC 6 H 4 NH 2. A colorless liquid, it is one of three isomers of fluoroaniline. It is used as a precursor to various potential and real applications. 4-Fluoroaniline can be prepared by the hydrogenation of 4-nitrofluorobenzene. [2]
It is one of three isomeric fluoronitrobenzenes. [2] A yellow oil, it is prepared from 4-nitrochlorobenzene using the Halex process: O 2 NC 6 H 4 Cl + KF → O 2 NC 6 H 4 F + KCl. 4-Fluoronitrobenzene can be hydrogenated to give 4-fluoroaniline, [3] which is a precursor to the fungicide fluoroimide and parafluorofentanyl.
2 BF 4 → ArF + N 2 + BF 3. Although hydrogen fluoride may appear to be an unlikely nucleophile, it is the most common source of fluoride in the synthesis of organofluorine compounds. Such reactions are often catalysed by metal fluorides such as chromium trifluoride.
This result suggested that there is a high selectivity for the 3° hydrogen, but the intermediate tertiary chloro compound 17 is rapidly solvolyzed. Similarly, no cyclic amine was observed with the reaction of n-amylisohexylamine, which demonstrates the selectivity for the 3° vs. 2° hydrogen migration.
4-Chloroaniline is used in the industrial production of pesticides, drugs, and dyestuffs. It is a precursor to the widely used antimicrobial and bacteriocide chlorhexidine and is used in the manufacture of pesticides, including pyraclostrobin , anilofos , monolinuron , and chlorphthalim .
Such procedures include Gattermann aldehyde synthesis, Houben-Hoesch ketone synthesis, and the Beckmann rearrangement. Their chemistry is related to that of enamines and their tautomers when the α hydrogen is next to the C=N bond. [1] Many chlorinated N-heterocycles are formally imidoyl chlorides, e.g. 2-chloropyridine, 2, 4, and 6 ...
H 2 C=CH 2 + HCl → CH 3 CH 2 Cl. In oxychlorination, hydrogen chloride instead of the more expensive chlorine is used for the same purpose: CH 2 =CH 2 + 2 HCl + 1 ⁄ 2 O 2 → ClCH 2 CH 2 Cl + H 2 O. Secondary and tertiary alcohols react with hydrogen chloride to give the corresponding chlorides.