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 
• 3115-68-2 tetrabutyl phosphonium bromide 
• 126-33-0 sulfolane 
• 81175-49-7 tetrakis(diethylamino)phosphonium bromide 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 541-73-1 1,3-Dichlorobenzene 
• 121-73-3 3-Nitrochlorobenzene 
• 144025-03-6 2,4-difluorophenylboronic acid 
• 367-25-9 2,4-difluorophenylamine 
• 2751-90-8 tetraphenylphosphonium bromide 
• 56022-38-9 triethyl-hexadecyl-phosphonium; bromide 
• 372-18-9 1,3-Difluorobenzene 
• 133117-48-3 1,3-difluoro-2-trimethylsilylbenzene 
• 148854-10-8 (2,4-difluorophenyl)trimethylsilane 

Downstream Products

• 76099-42-8 (2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-(5-fluoro-2-nitro-phenyl)-amine 
• 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 
• 133052-65-0 4-[(5-Fluoro-2-nitro-phenylamino)-methyl]-benzoic acid methyl ester 
• 446-38-8 2-fluoro-4-methoxy-1-nitro-benzene 
• 448-19-1 4-fluoro-2-methoxy-1-nitrobenzene 
• 28987-48-6 4-ethoxy-2-fluoro-1-nitrobenzene 
• 28987-44-2 5-fluoro-2-nitrophenyl ethyl ether 
• 28987-53-3 2-fluoro-1-nitro-4-phenoxy-benzene 
• 28987-52-2 4-fluoro-1-nitro-2-phenoxybenzene 
• 78227-85-7 2,4-bis(methylthio)nitrobenzene 
• 96631-28-6 2,4-diethoxy-1-nitro-benzene 
• 28987-46-4 4-fluoro-1-nitro-2-(propan-2-yloxy)benzene 
• 28987-50-0 2-fluoro-4-[(1-methylethyl)oxy]-1-nitrobenzene 

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.

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.

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)