70-34-8 Usage
Chemical Properties
Yellow solid
Uses
Different sources of media describe the Uses of 70-34-8 differently. You can refer to the following data:
1. 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.
2. 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.
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.
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
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 70-34-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 0 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 70-34:
(4*7)+(3*0)+(2*3)+(1*4)=38
38 % 10 = 8
So 70-34-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H3FN2O4/c7-4-2-1-3-5(8(10)11)6(4)9(12)13/h1-3H
70-34-8Relevant articles and documents
FORMATION OF FLUORO-MEISENHEIMER COMPLEXES USING HOMOGENEOUS AND HETEROGENEOUS FLUORIDE ION SOURCES
Clark, J. H.,Robertson, M. S.,Smith, D. K.,Cook, A.,Streich, C.
, p. 161 - 170 (1985)
1-Chloro-2,4-dinitrobenzene, 1-fluoro-2,4-dinitrobenzene and 1,3-dinitrobenzene form Meisenheimer complexes with tetra-n-butylammonium fluoride and alumina supported alkali metal fluorides.Both kinetically controlled and thermodynamically controlled complexes are observed.
CATALYTIC EFFECT OF DICYCLOHEXYL-18-CROWN-6-ETHER STEREOISOMERS IN THE SUBSTITUTION REACTIONS OF AROMATICALLY BOUND CHLORINE BY FLUORINE
Aksenov, V. V.,Vlasov, V. M.,Moryakina, I. M.,Rodionov, P. P.,Fadeeva, V. P.
, p. 629 - 630 (1987)
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Process for fluorinating inorganic or organic compounds by direct fluorination
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Paragraph 0326-0330, (2020/07/14)
The invention relates to the use of a fluorinated gas, wherein the elemental fluorine (F2) is present at a high concentration, the present invention relates to a process for producing fluorinated compounds by direct fluorination using a fluorination gas in which elemental fluorine (F2) is present at a high concentration, such as a concentration of elemental fluorine (F2), in particular equal to much higher than 15 vol% or even 20 vol% (i.e., at least 15 vol% or even 20 vol%), and to a process for producing fluorinated compounds by direct fluorination using a fluorination gas. The process of the present invention relates to the manufacture of fluorinated compounds other than fluorinated benzene by direct fluorination, in particular to the preparation of fluorinated organic compounds, end products and intermediates for use in agricultural, pharmaceutical, electronic, catalyst, solvent and other functional chemical applications. The fluorination process of the invention can be carried outin batches or in a continuous manner. If the process of the invention is carried out in batches, a column (tower) reactor may be used. If the process of the invention is continuous, a microreactor may be used.
Preparation and characterization of a novel silica-KF composite and facile fluorination of aromatic substrates
Patel, Sagar S.,Bochare, Machhindra D.,Degani, Mariam S.
, p. 20095 - 20100 (2018/12/13)
A novel silica-KF reagent prepared by hydrolyzing tetraethyl orthosilicate in the presence of KF for fluorination of activated aromatic compounds has been reported. The reagent, as characterized by techniques such as SEM-EDX, XRD and IR spectroscopy, is shown to have potassium cations entrapped inside the silica matrix whereas fluoride anions remain on the surface. Reaction of activated chlorinated aromatic substrates with this silica-KF leads to formation of Meisenheimer complex, either in situ or isolable, finally resulting in regioselective fluorinated aromatics.
Highly regioselective dinitration of toluene over reusable zeolite Hβ
Smith, Keith,Alotaibi, Mohammad Hayal,El-Hiti, Gamal A.
, p. 244 - 247 (2013/02/22)
A nitration system comprising nitric acid, propanoic anhydride, and zeolite Hβ has been developed for dinitration of toluene to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of over 120. This represents the most selective quantitative method for 2,4-dinitration of toluene; the catalyst is reusable, solvent is not needed, and an aqueous work-up is not required.
