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Chemical Compound Review:

MOLI001957 4-fluorophenol

Synonyms: AC1L9PKU, 4-fluoranylphenol

Bombek, S. et al., Battaini, G. et al., Graton, J. et al.

Graton, Berthelot, Besseau, Laurence,

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High impact information on MOLI001957

Whereas 3- and 4-fluorophenol react with tyrosinase to give products that undergo a rapid polymerization process, 2-fluorophenol is not reactive and actually acts as a competitive inhibitor in the enzymatic oxidation of 3,4-dihydroxyphenylalanine (L-dopa) [1].
Enthalpies of hydrogen bonding to a reference hydrogen-bond acceptor, 4-fluorophenol, have been determined in CCl4 and/or C2Cl(4 for ammonia and 68 primary, secondary, and tertiary amines [2].
The electrophilic amination of 2-fluorophenol, 4-fluorophenol, and 2-chlorophenol was observed to occur as a result of their treatment with diazenes 1-4 under mild reaction conditions in the presence of ZrCl(4) [3].

Biological context of MOLI001957

On the other hand, the 2-chloro-4-amino-substituted phenols obtained from the 4-fluorophenol seem to be formed in a process that involves an ipso amination, the complete removal of the fluorine atom, and the introduction of the chlorine atom [3].

References

Tyrosinase-catalyzed oxidation of fluorophenols. Battaini, G., Monzani, E., Casella, L., Lonardi, E., Tepper, A.W., Canters, G.W., Bubacco, L. J. Biol. Chem. (2002) [Pubmed]
An enthalpic scale of hydrogen-bond basicity. 3. Ammonia, primary, secondary, and tertiary amines. Graton, J., Berthelot, M., Besseau, F., Laurence, C. J. Org. Chem. (2005) [Pubmed]
Electrophilic amination of 4-fluorophenol with diazenes: a complete removal of the fluorine atom. Bombek, S., Pozgan, F., Kocevar, M., Polanc, S. J. Org. Chem. (2004) [Pubmed]

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