Fluorobenzaldehyde Explained

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. 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]

Notes and 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 . en . 44 . 2 . 291–298 . 10.1016/S0022-1139(00)83946-9 . 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 . 10.1080/14756360600642131 . 17194027 . 38700429 . 1475-6366. free .
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 . 10.1155/2010/956242 . 0973-4945. free .