Fluorophenols
Fluorophenols | ||||||||
Surname | 2-fluorophenol | 3-fluorophenol | 4-fluorophenol | |||||
other names | o -fluorophenol | m -fluorophenol | p -fluorophenol | |||||
Structural formula | ||||||||
CAS number | 367-12-4 | 372-20-3 | 371-41-5 | |||||
PubChem | 9707 | 9743 | 9732 | |||||
Molecular formula | C 6 H 5 FO | |||||||
Molar mass | 112.10 g mol −1 | |||||||
Physical state | liquid | firmly | ||||||
Melting point | 16.1 ° C | 8-12 ° C | 43-46 ° C | |||||
boiling point | 171-172 ° C | 176-178 ° C | 185 ° C | |||||
pK s value | 8.82 | 9.36 | 9.92 | |||||
GHS labeling |
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H and P phrases | 226-302-312-332 | 301-315-318 | 302-312-315-319-332-335 | |||||
no EUH phrases | no EUH phrases | no EUH phrases | ||||||
280 | 280-301 + 310-305 + 351 + 338 | 261-280-305 + 351 + 338 |
In chemistry, fluorophenols form a group of substances that are derived from both phenol and fluorobenzene . The structure consists of a benzene ring with attached hydroxyl group (–OH) and fluorine (–F) as substituents . Their different arrangement results in three constitutional isomers with the empirical formula C 6 H 5 FO.
presentation
The fluorophenols can be prepared from the fluoroanilines by boiling their diazonium salts .
properties
The 4-fluorophenol, which has the highest symmetry, has the highest melting point. The introduction of the fluorine atom changes the boiling point only slightly compared to phenol (182 ° C). Due to the −I effect of the fluorine substituent, the fluorophenols have a higher acidity than the phenol. The pK s values are therefore correspondingly lower (phenol: 9.99).
literature
- Wiktor Zierkiewicz, Danuta Michalska, Bogusłwa Czarnik-Matusewicz, Maria Rospenk: Molecular Structure and Infrared Spectra of 4-Fluorophenol: A Combined Theoretical and Spectroscopic Study , J. Phys. Chem. A , 2003 , 107 , pp. 4547-4554 ( doi: 10.1021 / jp022564q ; PDF ).
Individual evidence
- ↑ a b c data sheet 2-fluorophenol from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
- ↑ a b c data sheet 3-fluorophenol from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
- ↑ a b c data sheet 4-fluorophenol from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
- ↑ a b CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
- ^ Entry on phenol in the GESTIS substance database of the IFA , accessed on December 27, 2014(JavaScript required) .