Fluorobenzaldehyde

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, some of which have antimicrobial properties. ^{[2] [3]}

References

1. 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.