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
• Article Data: 28

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

Description

2,4-Difluoronitrobenzene is an organic compound with the chemical formula C6H3F2NO2. It is a yellow liquid that is known for its reactivity in nucleophilic aromatic substitution reactions. 2,4-Difluoronitrobenzene is characterized by the presence of two fluorine atoms at the 2nd and 4th positions of the benzene ring, along with a nitro group (-NO2) attached to the same ring.

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.

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.