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. Schiff bases containing halogenated aromatic rings exhibit antimicrobial properties.[2][3]

References

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.
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.
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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[:0-1] 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.