Chemistry:4-Fluorobenzoic acid
From HandWiki
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| Names | |||
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| Preferred IUPAC name
4-Fluorobenzoic acid | |||
| Other names
p-fluorobenzoic acid, para-fluorobenzoic acid, 4-fluoro-benzoic acid
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| Identifiers | |||
3D model (JSmol)
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| Properties | |||
| C7H5FO2 | |||
| Molar mass | 140.113 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 | ||
| GHS pictograms |  
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| GHS Signal word | danger | ||
| 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). | |||
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Tracking categories (test):
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.[2]
4-Fluorobenzoic acid has been observed to form by the aerobic biotransformation of 4-fluorocinnamic acid.[3]
See also
- 2-Fluorobenzoic acid, the ortho isomer
- 3-Fluorobenzoic acid, the meta isomer
References
- ↑ GHS: PubChem 9973
- ↑ G. Schiemann; W. Winkelmüller (1943). "p-Fluorobenzoic Acid". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv2p0299.; Collective Volume, 2, pp. 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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