Chemical Properties
Yellow solid
Uses
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.
Uses
A substituted benzene use in polypeptide sequencing (also referred to as Sanger’s reagent). Used in the derivitization of primary amines. Shown to inhibit the reductase activity of mitochondrial b-c1 complex isolated from beef heart mitochondria.
Definition
ChEBI: The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.
General Description
Clear yellow crystals or yellow crystalline solid.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Reacts with oxidizing agents . When air was admitted after vacuum evaporation of an ether peroxide solution, a violent explosion occurred. A halogenated aromatic nitro compound. Aromatic nitro compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.
Fire Hazard
2,4-Dinitrofluorobenzene is probably combustible.
Biochem/physiol Actions
1-Fluoro-2,4-dinitrobenzene is a contact-sensitizing hapten, commonly used in experimental studies on contact hypersensitivity, inducing itch model, and atopic dermatitis. Mast cell activation is a key step in the DNFB induced sensitivity. DNFB covalently binds to the N-terminal amino acid of the protein and aids in Sanger sequencing.
Contact allergens
DNFB is a strong skin irritant and a universal contact allergen. It is used as an intermediate in the synthesis of pesticides and pharmaceuticals such as flurbiprofen, a chemical reagent, and as a topical sensitizer for the treatment of alopecia areata
Safety Profile
Poison by ingestion,skin contact, and subcutaneous routes. A powerful irritant and vesicant. Mutation data
reported. Solutions in ether may explode
when evaporated* When heated to
decomposition it emits highly toxic fumes of
NOx and F-. See also NITRO
E COMPOUNDS of AROMATIC
HYDROCARBONS and FLUORIDES.
Purification Methods
Crystallise the reagent from Et2O or EtOH. Distil it in a vacuum through a Todd Column (p 11). If it is to be purified by distillation in vacuo, the distillation unit must be allowed to cool before air is allowed into the apparatus; otherwise the residue carbonises spontaneously and an EXPLOSION may occur. The material is a skin irritant and may cause serious dermatitis. [Beilstein 5 IV 742.]
