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

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

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

• 36556-48-6 2-Chloro-3,4-difluoroaniline 
• 2613-34-5 2,4-difluoro-3-chloro-aniline 
• 446-35-5 2,4-Difluoronitrobenzene 
• 62-53-3 aniline 
• 371-40-4 4-fluoroaniline 
• 7664-93-9 sulfuric acid 
• 1493-27-2 ortho-nitrofluorobenzene 
• 83164-33-4 N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide 
• 1481-68-1 5-chloro-2,4-difluoronitrobenzene 
• 1435-43-4 1-chloro-3,5-difluorobenzene 
• 611-06-3 2,4-dichloronitrobenzene 
• 541-73-1 1,3-Dichlorobenzene 
• 121-73-3 3-Nitrochlorobenzene 
• 332-07-0 bis-(4-fluorophenyl)diazene 

Downstream Products

• 2267-73-4 N-(4-chloro-phenyl)-N'-(2,4-difluoro-phenyl)-urea 
• 1978-86-5 1-(4-bromophenyl)-3-(2,4-difluorophenyl)thiourea 
• 129367-44-8 (2,4-Difluoro-phenyl)-methoxymethyl-amine 
• 127555-83-3 1-(2,4-Difluoro-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one 
• 107396-77-0 2-(2,4-Difluoro-phenyl)-4H-naphtho[1,8-cd]azepine-1,3-dione 
• 22494-42-4 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid 
• 96980-65-3 2-chloro-N-(2,4-difluorophenyl)acetamide 

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.

Efficient and recyclable bimetallic Co–Cu catalysts for selective hydrogenation of halogenated nitroarenes

Silica supported N-doped carbon layers encapsulating Co–Cu nanoparticles (Co1Cux@CN/SiO2) were prepared by a one-step impregnation of Co(NO3)2·6H2O, Cu(NO3)2·3H2O, urea and glucose, following in situ carbothermal reduction. Effects of Cu contents on the catalytic performance of the Co1Cux@CN/SiO2 catalysts were investigated for selective hydrogenation of p-chloronitrobenzene to p-chloroaniline. The Co1Cu0.30@CN/SiO2 with Cu/Co molar ratio of 0.30:1 presented much higher activity and stability than the monometallic Co@CN/SiO2 catalyst. The addition of Cu into Co1Cux@CN/SiO2 catalysts had favorable effects on the formation of highly active Co–N sites and N-doped carbon layer. The role of the N-doped carbon layer was to protect the Co from oxidation by air, and the Co1Cu0.30@CN/SiO2 could be reused for at least 12 cycles without decrease in catalytic efficiency. Mechanistic and in situ infrared studies revealed that the interaction effect between the Co and Cu atoms made the surface of Co highly electron rich, which decreased adsorption of halogen groups and resulting in the enhanced selectivity during chemoselective hydrogenation of halogenated nitroarenes for a wide scope of substrates.

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.

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)

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

Solvent-Controlled CO2 Reduction by a Triphos-Iron Hydride Complex

The selective reduction of CO2 is of high interest toward future applications as a C1-building block. Therefore, metal complexes that allow for the formation of specific CO2 reduction products under distinct reaction conditions are necessary. A detailed understanding of the CO2 reduction pathways on a molecular level is, however, required to help in designing catalytic platforms for efficient CO2 conversion with specific product formation. Reported herein is a unique example of a solvent-controlled reduction of CO2 using a Triphos-based iron hydride complex. In THF, CO2 reduction selectively leads to CO formation, whereas experiments in acetonitrile exclusively afford formate, HCOO-. In order to explain the experimental findings, theoretical calculations of the reaction pathways were performed and further demonstrate the importance of the applied solvent for a selective reduction of CO2.

Anion ligand promoted selective C-F bond reductive elimination enables C(sp2)-H fluorination

A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.

Synthesis of 2 - fluoro aniline compounds of the method

The invention discloses a method for synthesizing 2 - fluoro aniline compounds of the method, the method is: shown in formula Ia aniline compound of formula Ib α and β shown aniline compound as raw materials, through coupling reaction shown [...] azobenzene compound II, then the type II shown azobenzene compound with a palladium catalyst, fluorination reagent, additive, organic solvent, in the 30 - 150 °C temperature closed agitating the fluorination reaction, [...] compound of formula III, type III compounds are shown in the reaction under the action of a reducing [...] shown IV 2 - fluoro aniline compounds; this invention synthetic 2 - fluoro aniline compounds substrate wide adaptability, mild reaction conditions, the operation is simple, fluorinated and good selectivity, [...] aniline compounds is prepared by many drug molecule is an important intermediate and starting material, wide application prospects.

Method for producing 2,4-difluroaniline by virtue of solvent-free catalytic hydrogenation method

The invention provides a method for producing 2,4-difluroaniline by virtue of a solvent-free catalytic hydrogenation method. According to the method, 2,4-difluroaniline is prepared through catalytic hydrogenation in a high-pressure kettle by adding a catalyst and phosphate under a solvent-free condition. Compared with a solvent hydrogenation method in the past, the solvent-free hydrogenation method has the advantages that the reaction efficiency is greatly improved, the utilization rate of equipment is obviously increased, meanwhile, the energy consumption and equipment cost due to recycling of a solvent can be effectively avoided, the method is a pollution-free environment-friendly process, and the generation of a large number of wastewater and waste residues is effectively avoided. By utilizing a noble metal catalyst, namely Pt/C, the preparation is simple, the catalyst can be circularly used in the reaction, and the metal can be recycled, so that the production cost is further lowered; and by utilizing phosphate as a dehydrogenation inhibitor, the reaction conversion rate can be increased.

Amino pyrimidine compound and preparation method and application thereof

The invention relates to an amino pyrimidine compound and a preparation method and application thereof. The amino pyrimidine compound has a structure as shown in a formula I. The formula is shown in the description. The compound is an inhibitor of an epidermal growth factor receptor (EGFR) kinase. The invention further relates to a medicine composition comprising the compound, a preparation methodand application thereof in preparation of anti-tumor medicines.