Fluorophenols

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Fluorophenols
Surname 2-fluorophenol 3-fluorophenol 4-fluorophenol
other names o -fluorophenol m -fluorophenol p -fluorophenol
Structural formula Structure of 2-fluorophenol Structure of 3-fluorophenol Structure of 4-fluorophenol
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
02 - Highly / extremely flammable 07 - Warning
Caution
05 - Corrosive 06 - Toxic or very toxic
danger
07 - Warning
Caution
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

  1. ↑ a b c data sheet 2-fluorophenol from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
  2. ↑ a b c data sheet 3-fluorophenol from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
  3. ↑ a b c data sheet 4-fluorophenol from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
  4. ↑ a b CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
  5. ^ Entry on phenol in the GESTIS substance database of the IFA , accessed on December 27, 2014(JavaScript required) .