Fluorobenzaldehyde is a group of three constitutional isomers of fluorinated benzaldehyde.

Properties

The isomers differ in the location of the fluorine, but they have the same chemical formulas.

Fluorobenzaldehyde isomers
Name o-Fluorobenzaldehyde m-Fluorobenzaldehyde p-Fluorobenzaldehyde
Structure
Systematic name 2-Fluorobenzaldehyde 3-Fluorobenzaldehyde 4-Fluorobenzaldehyde
Molecular formula C7H5FO C7H5FO C7H5FO
Molar mass 124.11 g/mol 124.11 g/mol 124.11 g/mol
CAS number 446-52-6 456-48-4 459-57-4
EC number 207-171-2 207-266-9 459-57-4
Properties
Melting point -44.5°C -10°C
Boiling point 175°C 173°C 181°C
Flash point 55°C 56°C 56°C
Density 1.18 g/cm3 1.174 g/cm3 1.175 g/cm3

Preparation

The 4-fluorobenzaldehyde isomer can be produced by a halogen-exchange reaction with 4-chlorobenzaldehyde.[1]

Uses

Fluorobenzaldehyde can be used as a synthetic intermediate because the fluorine can be replaced via oxidation reaction.[1] Due to the aldehyde group, the fluorobenzaldehydes can be used to make a variety of schiff base compounds through a condensation reaction. Schiff bases containing halogenated aromatic rings exhibit antimicrobial properties.[2][3]

References

  1. 1 2 Yoshida, Yasuo; Kimura, Yoshikazu (1989-08-01). "An improved and practical synthesis of 4-fluorobenzaldehyde by halogen-exchange fluorination reaction". Journal of Fluorine Chemistry. 44 (2): 291–298. doi:10.1016/S0022-1139(00)83946-9. ISSN 0022-1139.
  2. ↑ Singh, Kiran (2006). "Antibacterial Co(II), Ni(II), Cu(II) and Zn(II) Complexes of Schiff bases Derived from Fluorobenzaldehyde and Triazoles". Journal of Enzyme Inhibition and Medicinal Chemistry. 21 (5): 557–562. doi:10.1080/14756360600642131. ISSN 1475-6366. PMID 17194027. S2CID 38700429.
  3. ↑ Patel, Ishwar J.; Parmar, Shailesh J. (2010). "Synthesis and Studies of Novel Optically Active Schiff's Base Derivatives and their Antimicrobial Activities". e-Journal of Chemistry. 7 (2): 617–623. doi:10.1155/2010/956242. ISSN 0973-4945.
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