446-35-5

Basic information

• Product Name: 2,4-Difluoronitrobenzene
• Synonyms: 1-Nitro-2,4-difluorobenzene;2,4-difluoro-1-nitro-benzen;2,4-Difluronitrobenzene;Benzene, 2,4-difluoro-1-nitro-;1,3-difluoro-4-nitrobenzene;2,4-DIFLUORO-1-NITROBENZENE;2,4-DIFLUORONITROBENZENE;2,4-DIFLUORO NITROBENZEN
• CAS NO: 446-35-5
• Molecular Formula: C₆H₃F₂NO₂
• Molecular Weight: 159.09
• EINECS: 207-167-0
• Product Categories: HALIDE;Aromatic Hydrocarbons (substituted) & Derivatives;Fluorine series;alkyl Fluorine| nitro-compound
• Mol File: 446-35-5.mol

Chemical Properties

• Melting Point: 9-10 °C(lit.)
• Boiling Point: 203-204 °C(lit.)
• Flash Point: 195 °F
• Appearance: yellow liquid
• Density: 1.451 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 0.331mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents. Combustible.
• BRN: 2048034
• CAS DataBase Reference: 2,4-Difluoronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Difluoronitrobenzene(446-35-5)
• EPA Substance Registry System: 2,4-Difluoronitrobenzene(446-35-5)

Safety Data

• Hazard Codes: T,Xi,Xn
• Statements: 25-36/37/38-23/24/25-20/21/22
• Safety Statements: 26-45-36/37/39-23
• RIDADR: UN 2810 6.1/PG 1
• WGK Germany: 3
• RTECS: CZ5730000
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 446-35-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,4-Difluoronitrobenzene is used as a key intermediate in the synthesis of various organic compounds, including:
2,4-difluoro-5-nitrobenzenesulfonic acid, which is produced through a sulfonation reaction. 2,4-Difluoronitrobenzene finds applications in the chemical industry for further synthesis of other derivatives.
(±)-Horsfiline, a naturally occurring compound with potential biological activities, which can be synthesized using 2,4-difluoronitrobenzene as a starting material.
Resin-bound 2-arylaminobenzimidazoles, which are used in various chemical and pharmaceutical applications.
Used in Pharmaceutical Industry:
2,4-Difluoronitrobenzene is used as a reactant in the preparation of 4-thiazolidinone derivatives, which are known for their antimicrobial properties. These derivatives can be employed as active ingredients in the development of new antimicrobial agents to combat various bacterial infections.
Used in Research and Development:
The nucleophilic aromatic substitution of 2,4-difluoronitrobenzene with morpholine has been investigated using a flow reactor with a simulated moving bed (SMB) chromatography module. This research contributes to the understanding of the reaction mechanisms and optimization of the process, which can be beneficial for the development of new synthetic routes and applications of 2,4-difluoronitrobenzene in the chemical and pharmaceutical industries.

Synthesis

KF with n-Hexadecyltrimethylammonium bromide as the PTC has been shown recently to work in dimethylformamide (DMF), important owing to the low cost16 of DMF.

Upstream product

• 611-06-3 2,4-dichloronitrobenzene 
• 98-95-3 nitrobenzene 
• 2369-13-3 3-fluoro-4-nitroaniline 
• 148854-10-8 (2,4-difluorophenyl)trimethylsilane 
• 133117-48-3 1,3-difluoro-2-trimethylsilylbenzene 
• 372-18-9 1,3-Difluorobenzene 
• 3115-68-2 tetrabutyl phosphonium bromide 
• 56022-38-9 triethyl-hexadecyl-phosphonium; bromide 
• 126-33-0 sulfolane 
• 81175-49-7 tetrakis(diethylamino)phosphonium bromide 
• 2751-90-8 tetraphenylphosphonium bromide 
• 367-25-9 2,4-difluorophenylamine 
• 144025-03-6 2,4-difluorophenylboronic acid 
• 121-73-3 3-Nitrochlorobenzene 

Downstream Products

• 53013-41-5 4-(2-nitro-5-piperidinophenyl)piperidine 
• 448-19-1 4-fluoro-2-methoxy-1-nitrobenzene 
• 4920-84-7 2,4-dimethoxynitrobenzene 
• 327-92-4 1,5-difluoro-2,4-dinitrobenzene 
• 367-25-9 2,4-difluorophenylamine 
• 322-68-9 4-fluoro-2-(phenylamino)nitrobenzene 
• 76099-42-8 (2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-(5-fluoro-2-nitro-phenyl)-amine 
• 133307-43-4 2-Ethyl-1-(5-fluoro-2-nitro-phenyl)-1H-imidazole 
• 116940-74-0 1-(5-fluoro-2-nitrophenyl)piperidine-2-carboxylic acid 
• 140381-68-6 N-(2-nitro-5-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 140381-72-2 N-(3-fluoro-4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 79291-42-2 Ethyl 3-(5-fluoro-2-nitroanilino)-1-methylpyrazole-4-carboxylate 
• 134485-96-4 1,1'-(1-nitrobenzene-2,4-diyl)bis(2-methyl-1H-imidazole) 
• 133052-65-0 4-[(5-Fluoro-2-nitro-phenylamino)-methyl]-benzoic acid methyl ester 

Relevant articles and documents

Inexpensive, Active KF for Nucleophilic Aromatic Displacement Reactions

The simple, and inexpensive process, of recrystallizing KF from a methanol solution by slow evaporation of the solvent, followed by drying at 100 deg C, results in a highly active form of KF.The surface area was increased 20 fold by this process.This pre-treated KF proved to be considerably more efficient as a source of fluoride ion than untreated KF in the conversion of 2,4-dichloronitrobenzene to 2,4-difluoronitrobenzene.It was observed to be more efficient than spray dried KF but was less efficient than KF supported on CaF2.The results of a kinetic analysis of the above reaction using the pre-treated KF point towards a solid-liquid interfacial mechanism.

Novel preparation method of 2, 4, 5-trifluorophenylacetic acid

The invention discloses a novel preparation method of 2, 4, 5-trifluorophenylacetic acid, which belongs to the technical field of preparation of medical intermediates, and comprises the following preparation steps: carrying out nitration reaction on sulfuric acid and m-dichlorobenzene to obtain an intermediate II; adding the intermediate II, a phase transfer catalyst and potassium fluoride into an aprotic solvent to obtain an intermediate III; performing hydrogenation reaction on the intermediate III to obtain an intermediate IV; carrying out diazotization reaction on the intermediate IV, nitrosyl sulfuric acid and sodium fluoborate to obtain an intermediate V; performing cracking reaction on the intermediate V to obtain an intermediate VI; carrying out reduction reaction on the intermediate VI, and then carrying out bromination reaction on the intermediate VI and liquid bromine to obtain an intermediate VII; subjecting the intermediate VII to a substitution reaction with diethyl malonate, and obtaining 2, 4, 5-trifluorophenylacetic acid after hydrolysis and purification. A novel synthesis route is provided, the problem that technological operation is tedious is solved, the requirements for reaction and operation conditions are low, anhydrous and oxygen-free reaction conditions are not needed, the method is suitable for industrial production, and the yield and purity are greatly improved.

Preparation method of fluorine-containing aryl compound

The invention relates to the field of organic synthesis, and especially relates to a preparation method of a fluorine-containing aryl compound. The invention provides a preparation method of a compound as shown in a formula 1. The preparation method comprises the following steps: fluorination reaction: reacting a compound as shown in a formula 2 with alkali metal fluoride in the presence of a phase transfer catalyst to prepare the compound as shown in the formula 1. According to the preparation method of the fluorine-containing aryl compound provided by the invention, a reaction system does not contain a solvent, the boiling point of the phase transfer catalyst is relatively high, solvent interference is avoided during rectification or short steaming after the reaction is finished, the distillation yield is high, and the product purity is good.

Novel manufacturing method of fluoro-aryl compounds and derivatives thereof

The invention relates to a novel method of manufacturing fluoro-aryl compounds and derivatives thereof, in particular, fluorobenzene and derivatives thereof. The production environment of the manufacturing method is environmentally friendly. The shortages of a conventional method are overcome through a simple and beneficial mode. Compared with the prior art, the provided method is more effective,more environmentally friendly, and more energy saving. The method is used to produce core fluorinated aromatic compounds, preferably, core fluorinated fluorobenzene. On one aspect, the invention provides a method, which is advantages in industry and uses HF and a halogenated benzene precursor to prepare fluorobenzene and hydrogen halide. Moreover, the invention provides chlorobenzene as the primary raw material to prepare fluorobenzene, which is an important material in industry, and a beneficial, unexpected and simple application of chlorobenzene. In the prior art, the provided application ofchlorobenzene is unknown.

Catalyst and application thereof in synthesis of aromatic fluorine compounds

The invention belongs to the field of catalyst preparation and application, and particularly relates to a catalyst and application thereof in synthesis of aromatic fluorine compounds. The nickel catalyst is dichloro-bis-(tri-cyclohexylphosphine) nickel, and the molecular formula of the nickel catalyst is Ni (Py3) 2Cl2. The nickel catalyst is applied to catalyzing inorganic fluoride to replace aromatic chloride to synthesize fluoride. The catalyst has the advantages of easily available reagents, simple catalyst synthesis, simple operation conditions, low reaction temperature, high reaction yield and less time consumption.

Efficient synthesis method of meta-fluoranisole (by machine translation)

The method is characterized by comprising the following steps: taking m-chloronitrobenzene as a raw material, carrying out high-temperature chlorination reaction, nitration reaction and fluorination reaction to obtain 2,4 - 2,4 -difluorobenzene and carrying out a methoxylation reaction with m-difluorobenzene as a raw material and carrying out methoxylation reaction to obtain m-fluorobenzyl ether; and the hydrogenation catalyst is a porous alumina loaded NiO-Co222O3-MoOO3 composite catalyst. The method disclosed by the invention is simple in process and high in product yield. (by machine translation)

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

A convenient room temperature ipso-nitration of arylboronic acid catalysed by molecular iodine using zirconium oxynitrate as nitrating species: An experimental and theoretical investigation

A simple and convenient protocol has been developed for ipso-nitration of arylboronic acid catalysed by molecular iodine at room temperature, using zirconium oxynitrate as the nitrating species. The protocol is applicable to electronically diverse aryl- and heteroarylboronic acid moieties under mild reaction conditions with good to excellent isolated yields. Furthermore, a theoretical investigation has been performed for the same reaction, and reaction profiles are modelled using modern density functional theory (DFT). DFT-based results support the experimentally observed results.

Click chemistry inspired facile synthesis and bioevaluation of novel triazolyl analogs of Ludartin

A convenient and modular synthesis involving diastereoselective Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction was carried out to furnish 1,4-disubstituted-1,2,3-triazoles of Ludartin. This reaction scheme involving Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction leading to the formation of triazolyl analogs is being reported for the first time. All the triazolyl products were characterised using spectral data analysis. Sulphorhodamine B cytotoxicity screening of the resulting products against a panel of five human cancerous cell-lines revealed that few of the analogs display promising broad spectrum cytotoxic effect. Among all the synthesized compounds, only 3q displayed the best cytotoxic effect with IC50 values of 12, 11, 38, 39 and 8.5 μM but less than the standard Ludartin (1) with IC50 values of 6.3, 7.4, 7.5, 6.9 and 0.5 μM against human neuroblastoma (T98G), lung (A-549), prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cell lines, respectively. The present synthesis was designed based on the previous literature reports of Ludartin as an aromatase inhibitor. Our work provides an initial study on structure-activity relationship of triazolyl analogs of sesquiterpene lactones in general and Ludartin (1) in particular.

Phosphonium ionic liquids as highly thermal stable and efficient phase transfer catalysts for solid-liquid Halex reactions

Trihexyl (tetradecyl) phosphonium tetrafluoroborate was found to be an active catalyst for the introduction of fluoride by nucleophilic aromatic substitution. With a decomposition temperature above 300 °C, this ionic liquid is suitable for reactions at high temperatures. The addition of 1 mol% of the ionic liquid relative to KF increased the initial rate for the fluorination of 1,2-dichloro-4-nitrobenzene six-fold compared to the uncatalysed reaction. The highest reaction rate was observed at 20 mol% ionic liquid relative to KF. Ease of handling without the need for stringent drying conditions and reuseability make this ionic liquid a useful phase transfer catalyst.