Fluorobenzaldehyde is a group of three constitutional isomers of fluorinated benzaldehyde.
Properties
editThe 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
editThe 4-fluorobenzaldehyde isomer can be produced by a halogen-exchange reaction with 4-chlorobenzaldehyde.[1]
Uses
editFluorobenzaldehyde 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]
4'-Fluorobenzaldehyde is used to make: sulindac, Synthetic raspberry (Polish),[4][5] FGIN-127, rosuvastatin, GF 73 (Paroxetine PLE method),[6] & rivoglitazone.
3'-Fluorobenzaldehyde is used to make: cinflumide, DFB [15332-10-2][7]
2'-Fluorobenzaldehyde is used to make: efaroxan
References
edit- 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.
- ↑ 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.
- ↑ Barbara GAWDZIK, PL224133B1 (2018).
- ↑ Barbara Gawdzik, et al. PL408591 (2015).
- ↑ Yu, Marvin S; Lantos, Ivan; Peng, Zhi-Qiang; Yu, J; Cacchio, Thomas (2000). "Asymmetric synthesis of (−)-paroxetine using PLE hydrolysis". Tetrahedron Letters. 41 (30): 5647–5651. doi:10.1016/S0040-4039(00)00942-4.
- ↑ Williams Jr., David; Lindsley, Craig (2005). "Discovery of Positive Allosteric Modulators of Metabotropic Glutamate Receptor Subtype 5 (mGluR5)". Current Topics in Medicinal Chemistry. 5 (9): 825–846. doi:10.2174/1568026054750290.
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