4-Fluoronitrobenzene

Last updated
4-Fluoronitrobenzene
4-Fluornitrobenzol.svg
Names
Other names
1-fluoro-4-nitrobenzene, 1-nitro-4-fluorobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.912 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-502-8
PubChem CID
UNII
  • InChI=1S/C6H4FNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H
    Key: WFQDTOYDVUWQMS-UHFFFAOYSA-N
  • C1=CC(=CC=C1[N+](=O)[O-])F
Properties
C6H4FNO2
Molar mass 141.101 g·mol−1
Appearanceyellow solid, melting near room temperature
Density 1.340 g/cm3
Melting point 22–24 °C (72–75 °F; 295–297 K)
Boiling point 206 °C (403 °F; 479 K)
Hazards
GHS labelling: [1]
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H301, H302, H312, H317, H331, H373, H412
P260, P261, P264, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P317, P319, P321, P330, P333+P313, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Fluoronitrobenzene is an organic compound with the formula FC6H4NO2. It is one of three isomeric fluoronitrobenzenes. [2] A yellow oil, it is prepared from 4-nitrochlorobenzene using the Halex process:

O2NC6H4Cl + KF → O2NC6H4F + KCl

4-Fluoronitrobenzene can be hydrogenated to give 4-fluoroaniline, [3] which is a precursor to the fungicide fluoroimide.

Owing to the presence of the electron withdrawing nitro group, the fluoride is a good leaving group in fluoronitrobenzenes. Thus reaction with phenoxide gives the mononitrodiphenylether. [4]

Related Research Articles

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In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Hydroiodic acid</span> Solution of hydrogen iodide (HI) in water

Hydroiodic acid is an aqueous solution of hydrogen iodide (HI). It is a strong acid, one that is ionized completely in an aqueous solution. It is colorless. Concentrated solutions are usually 48% to 57% HI.

In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ 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 used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H 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.

<span class="mw-page-title-main">Nitroimidazole</span> Chemical compound

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<span class="mw-page-title-main">Aromatic sulfonation</span>

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<i>o</i>-Phenylenediamine Chemical compound

o-Phenylenediamine (OPD) is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. It is isomeric with m-phenylenediamine and p-phenylenediamine.

<span class="mw-page-title-main">4-Aminophenol</span> Chemical compound

4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.

<span class="mw-page-title-main">Fluorenone</span> Chemical compound

Fluorenone is an organic compound with the chemical formula (C6H4)2CO. It is bright fluorescent yellow solid.

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<span class="mw-page-title-main">2-Nitroaniline</span> Chemical compound

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<span class="mw-page-title-main">4-Nitroaniline</span> Chemical compound

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.

<span class="mw-page-title-main">4-Nitrochlorobenzene</span> Chemical compound

4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including antioxidants commonly found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.

In organic chemistry, thiocarboxylic acids or carbothioic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form and a thiol form. These are sometimes also referred to as "carbothioic O-acid" and "carbothioic S-acid" respectively. Of these the thiol form is most common.

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4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

<span class="mw-page-title-main">2-Nitrochlorobenzene</span> Chemical compound

2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2. It is one of three isomeric nitrochlorobenzenes. It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups.

In chemistry, the Halex process is used to convert aromatic chlorides to the corresponding aromatic fluorides. The process entails Halide exchange, hence the name. The reaction conditions call for hot solution of the aryl chloride and anhydrous potassium fluoride. Typical solvents are dimethylsulfoxide, dimethylformamide, and sulfolane. Potassium chloride is generated in the process. The reaction is mainly applied to nitro-substituted aryl chlorides.

References

  1. "1-Fluoro-4-nitrobenzene". pubchem.ncbi.nlm.nih.gov.
  2. Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi : 10.1002/14356007.a17_411
  3. Jagadeesh, Rajenahally V.; Surkus, Annette-Enrica; Junge, Henrik; Pohl, Marga-Martina; Radnik, Jörg; Rabeah, Jabor; Huan, Heming; Schünemann, Volker; Brückner, Angelika; Beller, Matthias (2013). "Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines". Science. 342 (6162): 1073–1076. Bibcode:2013Sci...342.1073J. doi:10.1126/science.1242005. PMID   24288327. S2CID   11780985.
  4. Brewster, Ray Q.; Groening, Theodore (1934). "p-Nitrodiphenyl Ether". Organic Syntheses. 14: 66. doi:10.15227/orgsyn.014.0066.