366-99-4

Basic information

• Product Name: 3-Fluoro-4-methoxyaniline
• Synonyms: 4-AMINO-2-FLUOROANISOLE;3-FLUORO-P-ANISIDINE;3-FLUORO-4-ANISIDINE;3-FLUORO-4-METHOXYANILINE;3-Fluoro-4-Methoxyaniline 2-Fluoro-4-Aminoanisole;4-Amino-2-fluoroanisol;3-Fluoro-p-anisidine (NH2=1);3-Fluoro-4-methoxy-phenylamine
• CAS NO: 366-99-4
• Molecular Formula: C₇H₈FNO
• Molecular Weight: 141.14
• EINECS: -0
• Product Categories: Other fluorin-contained compounds;Anilines, Aromatic Amines and Nitro Compounds;Aniline;Miscellaneous;Anilines, Amides & Amines;Anisoles, Alkyloxy Compounds & Phenylacetates;Fluorine Compounds
• Mol File: 366-99-4.mol

Chemical Properties

• Melting Point: 81-83 °C(lit.)
• Boiling Point: 135 °C18 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: Light beige to yellow-brown/Crystalline Powder
• Density: 1.1382 (estimate)
• Vapor Pressure: 0.0184mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.18±0.10(Predicted)
• BRN: 2717083
• CAS DataBase Reference: 3-Fluoro-4-methoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoro-4-methoxyaniline(366-99-4)
• EPA Substance Registry System: 3-Fluoro-4-methoxyaniline(366-99-4)

Safety Data

• Hazard Codes: Xn,Xi,T
• Statements: 20/21/22-36/37/38-23/24/25
• Safety Statements: 26-37/39-45-38-36/37/39-28A
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 366-99-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoro-4-methoxyaniline is used as a reagent for the synthesis of novel leucine ureido derivatives, which have potent inhibitory activity against aminopeptidase N. This application is significant in the development of new drugs targeting specific enzymes, potentially leading to treatments for various diseases.
Used in Chronic Pain Treatment:
In the pharmaceutical industry, 3-Fluoro-4-methoxyaniline is also utilized in the synthesis of novel mGluR1 antagonists. These compounds are being investigated for their potential to treat chronic pain by modulating the activity of metabotropic glutamate receptor 1, offering a new approach to pain management.
Used in Chemical Synthesis:
3-Fluoro-4-methoxyaniline serves as an essential intermediate in the synthesis of various organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and material science industries. Its unique chemical structure allows for the creation of new molecules with specific properties and functions.

InChI:InChI=1/C7H8FNO/c1-10-7-3-2-5(9)4-6(7)8/h2-4H,9H2,1H3

Upstream product

• 455-93-6 2-fluoro-1-methoxy-4-nitrobenzene 
• 104-94-9 4-methoxy-aniline 
• 321-28-8 1-fluoro-2-methoxybenzene 
• 2357-52-0 3-fluoro-4-methoxyphenyl bromide 
• 452-10-8 2,4-difluoro-1-methoxybenzene 
• 590417-81-5 1-(3-fluoro-4-methoxyphenyl)ethan-1-ol 
• 455-91-4 1-(3-fluoro-4-methoxyphenyl)ethanone 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 5345-54-0 3-chloro-4-methoxyaniline 

Downstream Products

• 2806-13-5 3-fluoro-4-methoxy-N,N-dimethyl-aniline 
• 452-11-9 3-fluoro-4-methoxyphenol 
• 452-09-5 4-chloro-2-fluoro-1-methoxybenzene 
• 2357-52-0 3-fluoro-4-methoxyphenyl bromide 
• 3824-21-3 (3-fluoro-4-methoxyphenyl) iodide 
• 458-55-9 2-fluoro-4-nitroso-anisole 
• 452-15-3 N-(3-fluoro-4-methoxyphenyl)acetamide 
• 124623-37-6 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone 
• 881193-38-0 1-[4-(3-fluoro-4-methoxy-phenylamino)-6-phenyl-pyrimidine-2-yl]-piperidin-4-ol 
• 221218-33-3 3-fluoro-4-methoxyphenyl isocyanate 
• 195533-53-0 2-fluoro-1-methoxy-4-pentafluorophenyl-sulfonamidobenzene 
• 622369-38-4 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarbonitrile 
• 1026366-77-7 N-(3-fluoro-4-methoxy-phenyl)-3,4,5-trimethoxy-benzamide 
• 1025898-05-8 N-(3-fluoro-4-methoxy-phenyl)-3,4,5-trimethoxy-thiobenzamide 

Relevant articles and documents

Mechanochemical Transformation of CF3 Group: Synthesis of Amides and Schiff Bases

We communicate two mild, solvent-free mechanochemical coupling transformations of CF3 group with nitro compounds into amides or Schiff bases employing Ytterbia as a catalyst. This process proceeds via C?F bond activation, accompanied with utilisation of Si-based reductants/oxygen scavengers – reductants of the nitro group. The scope and limitations of the disclosed methodologies are thoroughly studied. To the best of our knowledge, this work is the first example of mechanical energy promoted transformation of the inert CF3 group into other functionalities. (Figure presented.).

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.

Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis

Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

ORGANIC REACTIONS CARRIED OUT IN AQUEOUS SOLUTION IN THE PRESENCE OF A HYDROXYALKYL(ALKYL)CELLULOSE OR AN ALKYLCELLULOSE

The present invention relates to a method of carrying out an organic reaction in aqueous solution in the presence of a hydroxyalkyl(alkyl)cellulose or an alkylcellulose.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.

4,5-dihydropyrazolo [3,4-c] pyridine-2-one spiro derivatives, its preparation method and application

Disclosed are a spirocyclic derivative of 4,5-dihydropyrazolo[3,4-c]pyridine-2-one as represented by general formula (I), preparation method and use thereof, the definition of each substituent in the compound of general formula (I) being the same as the definition in the description.

Novel bicyclic heterocyclic compounds, process for their preparation and compositions containing them

The present invention provides, among other things, new bicyclo heterocyclic compounds, compositions comprising these heterocyclic compounds, methods of making the heterocyclic compounds, and methods of using these heterocyclic compounds for treating a variety of conditions and disease states associated with, for example, cellular proliferation, inflammation, glycosidase expression, or the low expression of Perlecan.

Electrophilic aromatic fluorination with fluorine: meta-Directed fluorination of anilines

Anilines are mainly or selectively fluorinated in the meta-position with F2 when dissolved in triflic acid, sometimes in the presence of small quantities of antimony pentafluoride. The regioselectivity is increased when an electron-donating substituent is present at the para-position.