4-Fluorobenzoic acid
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| Names | |
|---|---|
| IUPAC name
4-Fluorobenzoic acid | |
| Systematic IUPAC name
4-Fluorobenzoic acid | |
| Other names
p-fluorobenzoic acid, para-fluorobenzoic acid, 4-fluoro-benzoic acid | |
| Identifiers | |
| 456-22-4 | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:20364 |
| ChemSpider | 9579 |
| ECHA InfoCard | 100.006.600 |
| EC Number | 207-259-0 |
| PubChem | 9973 |
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| Properties | |
| C7H5FO2 | |
| Molar mass | 140.11 g·mol−1 |
| Appearance | white solid |
| Density | 1.479 g/cm3 |
| Melting point | 184 °C (363 °F; 457 K) |
| Boiling point | 253.687 °C (488.637 °F; 526.837 K) at 760 mmHg |
| 1200 mg/L | |
| log P | 2.07 |
| Acidity (pKa) | 4.14 |
| Hazards | |
| Main hazards | Irritates lungs, eyes, skin |
| Flash point | 107.226 °C (225.007 °F; 380.376 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
4-Fluorobenzoic acid (p-fluorobenzoic acid) is an organic compound with the formula C7H5FO2. This colourless solid is a derivative of benzoic acid carboxylic acid. It is a synthetic intermediate.
Preparation
4-Fluorobenzoic acid is commercially available. It may be prepared via the Schiemann reaction, in which a 4-aminobenzoic acid, protected as the ethyl ester, is diazotised and then fluoride introduced using tetrafluoroborate. Hydrolysis of the ester converts it back to the free acid.[1]
4-Fluorobenzoic acid has been observed to form by the aerobic biotransformation of 4-fluorocinnamic acid.[2]
References
- ↑ G. Schiemann; W. Winkelmüller (1943). "p-Fluorobenzoic Acid". Org. Synth.; Coll. Vol., 2, p. 299
- ↑ Freitas Dos Santos, Luisa M.; Spicq, Arnaud; New, Anthony P.; Lo Biundo, Giuseppe; Wolff, Jean-Claude; Edwards, Andrew (2001). "Aerobic biotransformation of 4-fluorocinnamic acid to 4-fluorobenzoic acid". Biodegradation. 12 (1): 23–9. doi:10.1023/A:1011973824171. PMID 11693292.
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