70-34-8

Basic information

• Product Name: 2,4-Dinitrofluorobenzene
• Synonyms: 2,4-Dinitrofluorobenzene,98%;2,4-Dinitrofluoroben;4-Dinitrofluorobenzene;4-Fluoro-1,3-dinitrobenzene;NSC 33519;(T)2,4-DINITRO-1-FLUOROBENZENE;1,1′-Bis(1-dinaphthylphosphino)ferrocene;Zhou′s Ligand
• CAS NO: 70-34-8
• Molecular Formula: C₆H₃FN₂O₄
• Molecular Weight: 186.1
• EINECS: 200-734-3
• Product Categories: Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Organics;Fluorobenzene;Amino Group Labeling Reagents for HPLC;Analytical Chemistry;HPLC Labeling Reagents;UV Detection (HPLC Labeling Reagents);Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry
• Mol File: 70-34-8.mol

Chemical Properties

• Melting Point: 25-27 °C(lit.)
• Boiling Point: 178 °C25 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Yellow to brownish/Liquid or Low Melting Crystals
• Density: 1.482 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000207mmHg at 25°C
• Refractive Index: n20/D 1.569(lit.)
• Storage Temp.: 2-8°C
• Solubility: chloroform: 0.1 g/mL, clear
• Water Solubility: 400 mg/L (25 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,4172
• BRN: 398632
• CAS DataBase Reference: 2,4-Dinitrofluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dinitrofluorobenzene(70-34-8)
• EPA Substance Registry System: 2,4-Dinitrofluorobenzene(70-34-8)

Safety Data

• Hazard Codes: C,T,Xn
• Statements: 22-33-34-42/43-40-23/24/25-43-36/38-36/37/38
• Safety Statements: 22-26-36/37/39-45-28A-23-7/9-36/37
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: CZ7800000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 70-34-8(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry and Molecular Biology:
2,4-Dinitrofluorobenzene is used as a reagent for identifying the amino acid sequence in proteins. It reacts with the amino group of amino acids, yielding dinitrophenyl-amino acids, which can be further analyzed to determine the sequence. This application is particularly useful in polypeptide sequencing and the derivatization of primary amines.
Used in Chromatographic Methods:
In the field of analytical chemistry, 2,4-Dinitrofluorobenzene is employed in chromatographic techniques to separate and identify various compounds. Its unique chemical properties allow for the effective resolution of complex mixtures, making it a valuable tool in the study of chemical structures and interactions.
Used in Enzyme Inhibition Studies:
2,4-Dinitrofluorobenzene has been shown to inhibit the reductase activity of the mitochondrial b-c1 complex isolated from beef heart mitochondria. This application highlights its potential use in studying enzyme function and regulation, contributing to a deeper understanding of cellular processes and metabolic pathways.

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.]

InChI:InChI=1/C6H3FN2O4/c7-4-2-1-3-5(8(10)11)6(4)9(12)13/h1-3H

Upstream product

• 462-06-6 fluorobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 584-48-5 2,4-dinitrobromobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 602-02-8 2,3-dinitrochlorobenzene 
• 950487-33-9 3-(2,4-dinitrophenoxy)-3-fluoro-3H-diazirine 
• 99-65-0 meta-dinitrobenzene 
• 655-07-2 2,4-dinitro-1-(trifluoromethoxy)benzene 
• 100-39-0 benzyl bromide 
• 455-17-4 (p-fluorophenyl)trimethylsilane 

Downstream Products

• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 7061-92-9 1,4-bis(2,4-dinitrophenyl)piperazine 
• 14545-01-8 N-2,4-dinitrophenylimidazole 
• 124135-61-1 1,8-bis-(2,4-dinitro-phenyl)-1,8-diaza-cyclotetradecane 
• 40832-90-4 1-(2,4-Dinitrophenyl)-perhydroazepin 
• 99974-29-5 4-(2,4-dinitro-phenoxy)-3-methyl-5H-furan-2-one 
• 84165-39-9 8-(2,4-dinitro-phenoxy)-quinoline 
• 99989-94-3 5-(2,4-dinitro-phenoxymethyl)-2-methyl-pyrimidin-4-ylamine 
• 5920-71-8 1-(2,4-dinitro-phenyl)-3-(4-methoxy-phenyl)-4,5-dihydro-1H-pyrazole 
• 23309-20-8 1-(2,4-dinitro-phenyl)-4-methyl-1H-imidazole 
• 120233-13-8 1,8,15,22-tetrakis-(2,4-dinitro-phenyl)-1,8,15,22-tetraaza-cyclooctacosane 
• 107413-74-1 N-(2,4-dinitro-phenyl)-sulfanilic acid-[2]pyridylamide 
• 106477-36-5 N-(2,4-dinitro-phenyl)-sulfanilic acid thiazol-2-ylamide 
• 130862-49-6 N-(2,4-dinitro-phenyl)-sulfanilic acid-(4-methyl-thiazol-2-ylamide) 

Relevant articles and documents

FORMATION OF FLUORO-MEISENHEIMER COMPLEXES USING HOMOGENEOUS AND HETEROGENEOUS FLUORIDE ION SOURCES

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.

Reactions at solid-liquid interfaces. The mechanism and kinetics of the fluorination of 2,4-dinitrochlorobenzene using solid potassium fluoride in dimethylformamide

The halogen exchange reaction of 2,4-dichloronitrobenzene with potassium fluoride in dimethylformamide containing tetrabutylammonium salts has been studied employing an electrochemical detection methodology based upon the use of square wave voltammetry to follow the loss of reactant and the formation of the product and intermediates. The results obtained show that the kinetics of loss of parent material behave on one hand as a dissolution-rate-controlled process and on the other as a homogeneous chemical process. Initially homogeneous reaction dominates the observed kinetics as the presaturated solution is stripped of fluoride ion; at longer time, the observed kinetics are controlled by the rate of KF dissolution. Modeling the system using a fully implicit finite difference method with Richtmyer modification (FIRM algorithm) yielded a mean value for the homogeneous rate constant for the formation of 2,4-dinitrofluorobenzene by reaction of 2,4-dichloronitrobenzene with fluoride ion in DMF at 85 ?°C of 640 ?± 250 mol-1 cm3 s-1 and a mean value for the saturation concentration of fluoride ion of (6.5 ?± 0.5) ?? 10-6 mol cm-3. Ultrasound was found not to significantly enhance the rate of the reaction in the intensity range studied. Furthermore, the utility of microelectrodes for obtaining simple quantifiable voltammetric responses from compounds of which the macroelectrode responses are complicated by chemical followup steps is demonstrated. Ultrasonically induced mixing has been shown to facilitate reproducible microelectrode responses in intrinsically heterogeneous systems.

A rings-in-pores net: Crown ether-based covalent organic frameworks for phase-transfer catalysis

We herein present a new family of crown ether-based covalent organic frameworks (CE-COFs) for the first time. The CE-COFs show excellent phase-transfer catalytic performance in various nucleophilic substitution reactions.

Process for fluorinating inorganic or organic compounds by direct fluorination

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

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.

Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems

Various nitration systems comprising nitric acid, acid anhydride and zeolite H￡] in the absence of solvent are described. Direct double nitration of toluene with a nitric acid, propanoic anhydride and zeolite Hβ system has been developed to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of 123:1. This system also nitrates activated mono-substituted benzenes (anisole and phenetole) and moderately activated mono-substituted benzenes (ethylbenzene and propylbenzene) to give mainly 2,4-dinitro derivatives. The zeolite can be recovered, regenerated and reused to give almost the same yield as that given when fresh zeolite is used. ARKAT-USA, Inc.

Highly regioselective dinitration of toluene over reusable zeolite Hβ

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.

METHODS FOR THE NITRATION OF AROMATIC COMPOUNDS

According to the invention there is provided a method for the nitration of an aromatic compound including the step of reacting the aromatic compound with nitric acid in the presence of an acid anhydride and an aluminosilicate catalyst, in which the acid anhydride is at least one of: ((CnH2n+1)CO)20, where n is 1 to 4 and the moiety CnH2n+1 can be straight or branched chain; ((CHpClq)CO)20, where p is 0 to 2, q is 1 to 3, and p+q = 3; and oxoiane -2, 5-dione, with the proviso that when the acid anhydride is (CH3CO)20, the aromatic compound is toluene, 2-nitrotoluene or 4-nitrotoluene, and the nitration is performed to produce 2,4-dinitrotoluene.

BORON OR ALUMINUM COMPLEXES

The present invention relates to boron and aluminum complexes, to the preparation thereof, and to the use thereof for solubilizing ionic compounds. The complexes have one of the following formulae: in which D represents B or Al; R1 represents R, RF, NO2, CN, C(═O)OR, RSO2, or RFSO2; —X1—, —X2—, —X3— and X4 each represent a divalent group >C═O, >C═NC≡N, >C═C(C≡N)2, >CR2R3 or >SO2; —Y1—, —Y2— and —Y3— each represent a divalent group —O—, >N(C≡N), >N(CORF), >N(SO2R4), >NR4, >N(COR4) or >N(SO2RF); R, R2 and R3 each represent H, an alkyl group, an aryl group, an alkylaryl group, an arylalkyl group, an oxaalkyl group or an alkenyl group; R4 represents an alkyl group, an aryl group, an alkylaryl group, a heteroaryl group, an arylalkyl group, an oxaalkyl group, an alkenyl group or an RFCH2— group; RF is a perfluoroalkyl group, a partially fluorinated alkyl group, or a partially or totally fluorinated phenyl group; each of the R′2 and R′3 groups represents R or F.

Di(1H,1H,2H,2H-perfluorooctyl)-dibenzo-18-crown-6: A "light fluorous" recyclable phase transfer catalyst

A series of dibenzo-18-crown-6 lariat ethers containing two C 7H15 (11), (CH2)2C6F 13 (14), (CH2)2C8F17 (15), NHC7H15 (18) and NHCH2C6F 13 (19) sidearms were prepared and the single crystal X-ray structure of cis-4,4′-di(1H,1H,2H,2H-perfluorodecyl)-dibenzo-18-crown-6 (15a) is reported. The "light fluorous" dibenzo-18-crown-6 ether (14) has emerged as a stable and robust PTC catalyst, which can be recycled efficiently by fluorous solid-phase extraction, and gives better PTC catalytic activity compared to the parent, non-fluorinated PTC catalyst, dibenzo-18-crown-6, and the alkylated derivative (11) in aliphatic and aromatic nucleophilic substitutions.