456-49-5

Basic information

• Product Name: 3-Fluoroanisole
• Synonyms: M-FLUORO METHOXYBENZENE;M-FLUOROANISOLE;1-Fluoro-3-methoxybenzene;1-fluoro-3-methoxy-benzene;Benzene, 1-fluoro-3-methoxy-;3-Fluoroanisole,99%;3-Fluoroanisole 99%;m-Fluorophenyl methyl ether
• CAS NO: 456-49-5
• Molecular Formula: C₇H₇FO
• Molecular Weight: 126.13
• EINECS: 207-267-4
• Product Categories: Other fluorin-contained compounds;AnisoleSeries;Fluorobenzene;Anisoles, Alkyloxy Compounds & Phenylacetates;Fluorine Compounds;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 456-49-5.mol

Chemical Properties

• Melting Point: -35°C
• Boiling Point: 158 °C743 mm Hg(lit.)
• Flash Point: 111 °F
• Appearance: clear colorless to straw yellow liquid
• Density: 1.104 g/mL at 25 °C(lit.)
• Vapor Pressure: 38.3mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Storage Temp.: Flammables area
• Solubility: Chloroform, Methanol
• BRN: 1858895
• CAS DataBase Reference: 3-Fluoroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoroanisole(456-49-5)
• EPA Substance Registry System: 3-Fluoroanisole(456-49-5)

Safety Data

• Hazard Codes: F
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 456-49-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoroanisole is used as a synthetic intermediate for the preparation of tertiary benzylic nitriles, which are important building blocks in the synthesis of various pharmaceutical compounds. These nitriles can be further converted into amines, amides, and other functional groups, contributing to the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
3-Fluoroanisole is utilized in the synthesis of various organic compounds, such as 4-fluoro-5,6-dihydroxytryptamine, 3-fluoro-, and 5-fluoronoradrenaline. These synthesized compounds are valuable for studying the structure-activity relationships of biologically active molecules and can be used as probes in understanding the mechanisms of various biological processes.

InChI:InChI=1/C7H5F3O/c8-7(9,10)11-6-4-2-1-3-5-6/h1-5H

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 10365-98-7 3-methoxyphenylboronic acid 
• 79421-99-1 tris(3-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 536-90-3 m-Anisidine 
• 100-66-3 methoxybenzene 
• 372-20-3 3-fluorophenol 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 367-25-9 2,4-difluorophenylamine 
• 5509-65-9 2,6-difluoroaniline 
• 372-18-9 1,3-Difluorobenzene 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 

Downstream Products

• 372-20-3 3-fluorophenol 
• 394-18-3 1-fluoro-5-methoxy-2,4-dinitrobenzene 
• 2113-56-6 3-methoxybiphenyl 
• 379-37-3 (2-fluoro-6-methoxy-phenyl)-diphenyl-methanol 
• 458-50-4 1-bromo-2-fluoro-4-methoxybenzene 
• 52872-61-4 (2-fluoro-4-methoxy-phenyl)-(5-nitro-thiazol-2-yl)-methanone 
• 331-64-6 2-fluoro-4-methoxy-benzaldehyde 
• 146137-74-8 2-fluoro-6-methoxybenzaldehyde 
• 151-10-0 1,3-Dimethoxybenzene 
• 129448-63-1 1-(2-fluoro-4-methoxyphenyl)-2-phenylethanone 
• 92262-31-2 2-fluoro-4-methoxy-α-(trans-4-propylcyclohexane)acetophenone 
• 92262-30-1 2-fluoro-4-methoxy-α-(trans-4-pentylcyclohexane)acetophenone 
• 92262-32-3 2-fluoro-4-methoxy-α-(trans-4-heptylcyclohexane)acetophenone 
• 448-19-1 4-fluoro-2-methoxy-1-nitrobenzene 

Relevant articles and documents

A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen

Hydrodehalogenation is an effective strategy for transforming persistent and potentially toxic organohalides into their more benign congeners. Common methods utilize Pd/C or Raney-nickel as catalysts, which are either expensive or have safety concerns. In this study, a nickel-based catalyst supported on titania (Ni-phen@TiO2-800) is used as a safe alternative to pyrophoric Raney-nickel. The catalyst is prepared in a straightforward fashion by deposition of nickel(II)/1,10-phenanthroline on titania, followed by pyrolysis. The catalytic material, which was characterized by SEM, TEM, XRD, and XPS, consists of nickel nanoparticles covered with N-doped carbon layers. By using design of experiments (DoE), this nanostructured catalyst is found to be proficient for the facile and selective hydrodehalogenation of a diverse range of substrates bearing C?I, C?Br, or C?Cl bonds (>30 examples). The practicality of this catalyst system is demonstrated by the dehalogenation of environmentally hazardous and polyhalogenated substrates atrazine, tetrabromobisphenol A, tetrachlorobenzene, and a polybrominated diphenyl ether (PBDE).

Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination

Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the substrate scope as well as the scope of suitable reactions that can sustain such conditions. Numerous reactions, for example, decarboxylative fluorination that is well developed for aliphatic carboxylic acids, are out of reach for the aromatic counterparts with current reaction chemistry. Here, we report a conceptually different approach through a low-barrier photoinduced ligand to metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation strategy, which generates a putative high-valent arylcopper(III) complex, from which versatile facile reductive eliminations can occur. We demonstrate the suitability of our new approach to address previously unrealized general decarboxylative fluorination of benzoic acids.

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)

Fluorination of arylboronic esters enabled by bismuth redox catalysis

Bismuth catalysis has traditionally relied on the Lewis acidic properties of the element in a fixed oxidation state. In this paper, we report a series of bismuth complexes that can undergo oxidative addition, reductive elimination, and transmetallation in a manner akin to transition metals. Rational ligand optimization featuring a sulfoximine moiety produced an active catalyst for the fluorination of aryl boronic esters through a bismuth (III)/bismuth (V) redox cycle. Crystallographic characterization of the different bismuth species involved, together with a mechanistic investigation of the carbonfluorine bond-forming event, identified the crucial features that were combined to implement the full catalytic cycle.

Reactions of Arylsulfonate Electrophiles with NMe4F: Mechanistic Insight, Reactivity, and Scope

This paper describes a detailed study of the deoxyfluorination of aryl fluorosulfonates with tetramethylammonium fluoride (NMe4F) and ultimately identifies other sulfonate electrophiles that participate in this transformation. 19F NMR spectroscopic monitoring of the deoxyfluorination of aryl fluorosulfonates revealed the rapid formation of diaryl sulfates under the reaction conditions. These intermediates can proceed to fluorinated products; however, diaryl sulfate derivatives bearing electron-donating substituents react very slowly with NMe4F. Based on these findings, aryl triflate and aryl nonaflate derivatives were explored, since these cannot react to form diaryl sulfates. Aryl triflates were found to be particularly effective electrophiles for deoxyfluorination with NMe4F, and certain derivatives (i.e., those bearing electron-neutral/donating substituents) afforded higher yields than their aryl fluorosulfonate counterparts. Computational studies implicate a similar mechanism for deoxyfluorination of all the sulfonate electrophiles.

Application of trivalent iodine compounds as catalysts in Bal-Schiemann reaction

The invention discloses an application of trivalent iodine compounds shown in formula I and/or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

Transition metal free, late-stage, regiospecific, aromatic fluorination on a preparative scale using a KF/crypt-222 complex

We herein report the development of a convenient, regioselective, aromatic fluorination method of hypervalent iodonium ylides for synthesising fluoro-arenes on a preparative scale. This transition metal free, nucleophilic methodology provides good yields for sterically hindered substrates, irrespective of activation. The methodology simplifies reference synthesis for PET imaging.

METHOD FOR AROMATIC FLUORINATION

Disclosed is a fluorination method comprising providing an aryl fluorosuifonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosuifonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxyiate, and SO2F2 to a reaction mixture; reacting the SO2F2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar-OH to a reaction mixture; where A is an aryl or heteroaryl; providing SO2F2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO2F2, the fluorinating reagent and the compound having the structure Ar-OH to provide a fluorinated aryl species having the structure Ar-F.

Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion

Pioneering studies by Kuivila, published more than 50 years ago, suggested ipso protonation of the boronate as the mechanism for base-catalyzed protodeboronation of arylboronic acids. However, the study was limited to UV spectrophotometric analysis under acidic conditions, and the aqueous association constants (Ka) were estimated. By means of NMR, stopped-flow IR, and quenched-flow techniques, the kinetics of base-catalyzed protodeboronation of 30 different arylboronic acids has now been determined at pH > 13 in aqueous dioxane at 70 °C. Included in the study are all 20 isomers of C6HnF(5-n)B(OH)2 with half-lives spanning 9 orders of magnitude: a and Sδ values, kinetic isotope effects (2H, 10B, 13C), linear free-energy relationships, and density functional theory calculations, we have identified a mechanistic regime involving unimolecular heterolysis of the boronate competing with concerted ipso protonation/C-B cleavage. The relative Lewis acidities of arylboronic acids do not correlate with their protodeboronation rates, especially when ortho substituents are present. Notably, 3,5-dinitrophenylboronic acid is orders of magnitude more stable than tetra-and pentafluorophenylboronic acids but has a similar pKa.