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1-Fluoro-2,4-dinitrobenzene is used to identify the amino acid sequence. It reacts with amino group of amino acids to yield dinitrophenyl-amino acids. It is also used in chromatographic methods. Further, it acts as an alkylating agent used in elucidating amino acid sequence in proteins.
The activated fluoro-substituent is readily displaced by nucleophiles under mild conditions. The anomeric center of a carbohydrate has been protected as the 2,4-dinitrophenyl ether in the presence of DABCO in DMF: Rec. Trav. Chim., 99, 355 (1980).
Used for labelling terminal amino acids in peptides: Biochem. J., 45, 563 (1949); Biochemistry, 20, 512 (1981).
Has been used as a means of protection for the thiol group. The resulting thioether can be cleaved quantitatively with 2-mercaptoethanol: Biochem. Biophys. Res. Commun., 29, 178 (1967).
Can also be used for the masking of the imidazole ring in histidine as the 2,4-dinitrophenyl derivative during peptide synthesis, introduced in the presence of, e.g. K2CO3: Biochem. Biophys. Acta., 82, 412 (1964). The group can be cleaved by treatment with thioglycolic acid, mercaptoethanol, dithiothreitol or thiophenol: Biochem. Biophys. Res. Commun., 29, 178 (1967); Biochemistry, 9, 5122 (1970). The electron withdrawing character of the group has been shown to reduce racemization promoted by the imidazole function: J. Biol. Chem., 247, 4768 (1972). See Appendix 6.
Harifi-Mood, A. R.; Faramarzi, F.; Mehrabi, Y. Investigation of solvent effects on the reaction of 1-fluoro-2,4-dinitrobenzene with aniline in molecular-molecular and ionic liquid-molecular solvent mixtures. Prog. React. Kinet. Mec. 2015, 40 (1), 35-47.
Jalalizadeh, H.; Raei, M.; Tafti, R. F.; Farsam, H.; Kebriaeezadeh, A.; Souri, E. A Stability-Indicating HPLC Method for the Determination of Memantine Hydrochloride in Dosage Forms through Derivatization with 1-Fluoro-2,4-dinitrobenzene. Sci. Pharm. 2014, 82 (2), 265-279.
Gefahrenhinweise (EU): H301-H311-H331-H315-H318-H317-H341
Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye damage. May cause an allergic skin reaction. Suspected of causing genetic defects.
Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.