367-25-9

Basic information

• Product Name: 2,4-Difluoroaniline
• Synonyms: 2,4-difluoro-anilin;Aniline, 2,4-difluoro-;Benzenamine, 2,4-difluoro-;LABOTEST-BB LTBB000653;AKOS 91127;2,4-DIFLUOROPHENYLAMINE;2,4-DIFLUOROBENZENAMINE;1-amino-2,4-difluorobenzene
• CAS NO: 367-25-9
• Molecular Formula: C₆H₅F₂N
• Molecular Weight: 129.11
• EINECS: 206-687-5
• Product Categories: Fluorobenzene Series;Anilines, Aromatic Amines and Nitro Compounds;pharmacetical;Aniline;Fluorobenzene;Amines;C2 to C6;Nitrogen Compounds;Fluorine series
• Mol File: 367-25-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: −7.5 °C(lit.)
• Boiling Point: 170 °C753 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: Clear brown/Liquid
• Density: 1.268 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.8mmHg at 25°C
• Refractive Index: n20/D 1.506(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Not miscible or difficult to mix.
• PKA: 3.26±0.10(Predicted)
• Water Solubility: 1-5 g/100 mL at 20.55 ºC
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.
• Merck: 14,3147
• BRN: 2802556
• CAS DataBase Reference: 2,4-Difluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Difluoroaniline(367-25-9)
• EPA Substance Registry System: 2,4-Difluoroaniline(367-25-9)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 28-36/37/39-26-36
• RIDADR: UN 2941 6.1/PG 3
• WGK Germany: 1
• RTECS: BX3680000
• F: 8-9-23
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 367-25-9(Hazardous Substances Data)

Usage

Description

2,4-Difluoroaniline, also known as 2,4-difluoro-1-aminobenzene, is an organic compound that belongs to the class of aromatic amines. It is characterized by the presence of two fluorine atoms at the 2nd and 4th positions of the benzene ring, with an amino group attached to the 1st position. 2,4-Difluoroaniline is a dark reddish-purple liquid and is widely recognized for its significance as an intermediate in various chemical syntheses.

Uses

Used in Organic Synthesis:
2,4-Difluoroaniline is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure, with fluorine atoms and an amino group, allows for a range of reactions and functional group transformations, making it a versatile building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-difluoroaniline is utilized as a starting material for the development of new drugs and active pharmaceutical ingredients. Its chemical properties enable the creation of novel drug candidates with potential therapeutic applications, contributing to the advancement of medicinal chemistry.
Used in Agrochemicals:
2,4-Difluoroaniline is also employed in the agrochemical sector as a precursor for the synthesis of various pesticides, herbicides, and other crop protection agents. Its incorporation into these chemicals can enhance their efficacy, selectivity, and environmental compatibility, ultimately benefiting agricultural productivity and sustainability.
Used in Dye Industry:
The dye industry leverages 2,4-difluoroaniline as a crucial intermediate for the production of a wide array of dyes and pigments. 2,4-Difluoroaniline's ability to form various chromophores and its compatibility with different dye classes make it an essential component in the development of new colorants for textiles, plastics, and other applications.
Used in Agricultural Chemicals:
In the agricultural chemicals sector, 2,4-difluoroaniline serves as a vital intermediate for the synthesis of various agrochemicals, including plant growth regulators, insecticides, and fungicides. Its role in the development of these products helps improve crop yield, quality, and resistance to pests and diseases, supporting global food security and agricultural sustainability.

Reference

R. Garth Pews, J. A. Gall, Process and intermediates for the preparation of 2,6-difluoroaniline, Paten US5041674A

Air & Water Reactions

2,4-Difluoroaniline may be sensitive to prolonged exposure to air. . Water soluble.

Reactivity Profile

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: 2,4-Difluoroaniline may be irritating to tissues.

Fire Hazard

2,4-Difluoroaniline is combustible.

InChI:InChI=1/C6H5F2N/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

Upstream product

• 446-35-5 2,4-Difluoronitrobenzene 
• 1435-43-4 1-chloro-3,5-difluorobenzene 
• 1481-68-1 5-chloro-2,4-difluoronitrobenzene 
• 83164-33-4 N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide 
• 1493-27-2 ortho-nitrofluorobenzene 
• 7664-93-9 sulfuric acid 
• 371-40-4 4-fluoroaniline 
• 62-53-3 aniline 
• 89-69-0 2,4,5-Trichloronitrobenzene 
• 108-70-3 1,3,5-trichlorobenzene 
• 36556-48-6 2-Chloro-3,4-difluoroaniline 
• 2613-34-5 2,4-difluoro-3-chloro-aniline 
• 3847-58-3 2,4-difluoro-3-chloro-nitrobenzene 
• 88-73-3 2-Chloronitrobenzene 

Downstream Products

• 1581-06-2 2.2'.4.4'-Tetrafluor-diphenyl-harnstoff 
• 366-46-1 hydroxyimino-acetic acid-(2,4-difluoro-anilide) 
• 367-27-1 2,4-difluorophenol 
• 2265-93-2 2,4-difluoro-1-iodobenzene 
• 444-14-4 2-bromo-4,6-difluoroaniline 
• 399-36-0 N-(2,4-difluoro-phenyl)-acetamide 
• 2267-73-4 N-(4-chloro-phenyl)-N'-(2,4-difluoro-phenyl)-urea 
• 368-01-4 N-(2,4-difluoro-phenyl)-N'-phenyl-urea 
• 1978-86-5 1-(4-bromophenyl)-3-(2,4-difluorophenyl)thiourea 
• 68904-76-7 C₁₄H₁₃F₄N₂PS₂ 
• 1933-73-9 bis(2,4-difluorophenylsulfonyl)methane 
• 68923-33-1 C₁₃H₁₁F₄N₂PS₂ 
• 57729-98-3 2,4-difluoro-2',4'-dinitro-6'-(trifluoromethyl)diphenylamine 
• 68904-77-8 C₁₆H₁₇F₄N₂PS₂ 

Relevant articles and documents

Synthesis of carbon-supported Pd/SnO2 catalyst for highly selective hydrogenation of 2,4-difluoronitrobenzene

Halogenated anilines have a wide range of applications in the production of pharmaceuticals and agrochemical substances, and thus it is of great importance to develop highly active and selective catalysts for the hydrogenation of halogenated nitrobenzenes. We approach this challenge by probing noble metal/non-noble metal oxide nanoparticles (NPs) catalysts. Carbon-supported Pd/SnO2 catalysts were synthesized by the chemical reduction method, and their catalytic activity was evaluated by the hydrogenation reaction of 2,4-difluoronitrobenzene (DFNB) to the corresponding 2,4-difluoroaniline (DFAN), showing a remarkable synergistic effect of the Pd and SnO2 NPs. The as-prepared Pd/SnO2/C catalysts were characterized using TEM, XRD, H2 TPD and XPS techniques. Modifications to the electronic structure of the Pd atoms through the use of SnO2 led to the suppression of the hydrogenolysis of the CF bond and the acceleration of nitrosobenzene (DFNSB) conversion and consequently, resulted in the inhibition of the formation of reactive by-products and may be responsible for the enhancements observed in selectivity.

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.

Highly selective hydrogenation of halogenated nitroarenes over Ru/CN nanocomposites by: In situ pyrolysis

A highly chemoselective and recyclable ruthenium catalyst for the hydrogenation of halogenated nitroarenes has been prepared via the simple in situ calcination of a mixture of melamine, glucose and ruthenium trichloride. Superfine Ru particles (2.3 ± 0.3 nm) were obtained and highly dispersed in the nitrogen-doped carbon matrix. The Ru/CN catalyst smoothly transforms a variety of halogenated nitroarenes to the corresponding haloanilines with high intrinsic activity (e.g. TOF = 1333 h-1 for p-chloronitrobenzene) and selectivity of more than 99.6percent. Furthermore, through an analysis of the products in the reaction process, it was concluded that there are two parallel reaction pathways (a direct pathway and an indirect pathway) for the hydrogenation of aromatic nitro compounds over the Ru/CN catalyst, and the direct pathway was proved to be dominant in catalyzing the intermediates. This journal is