399-55-3

Basic information

• Product Name: 2-FLUORO-4-METHYLANISOLE
• Synonyms: 2-FLUORO-4-METHYLANISOLE;2-Fluoro-1-methoxy-4-methylbenzene
• CAS NO: 399-55-3
• Molecular Formula: C₈H₉FO
• Molecular Weight: 140.15
• Mol File: 399-55-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 72 °C
• Flash Point: 63 °C
• Appearance: /
• Density: 1.046 g/cm³
• Vapor Pressure: 1.18mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: 2-FLUORO-4-METHYLANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORO-4-METHYLANISOLE(399-55-3)
• EPA Substance Registry System: 2-FLUORO-4-METHYLANISOLE(399-55-3)

Safety Data

• Hazardous Substances Data: 399-55-3(Hazardous Substances Data)

Usage

General Description

2-Fluoro-4-methylanisole is a chemical compound with the molecular formula C8H9FO and a molecular weight of 138.16 g/mol. It is a colorless liquid with a sweet, floral odor and is commonly used as a fragrance ingredient in the production of perfumes and other scented products. 2-FLUORO-4-METHYLANISOLE is also used in the manufacturing of pharmaceuticals, agrochemicals, and other specialty chemicals. It is important to handle this chemical with care, as it may cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Additionally, it should be stored in a cool, dry, well-ventilated area away from sources of heat and ignition.

InChI:InChI=1/C8H9FO/c1-6-3-4-8(10-2)7(9)5-6/h3-5H,1-2H3

Upstream product

• 50868-72-9 5-methoxy-o-toluidine 
• 104-93-8 p-methylanizole 
• 77153-73-2 2-Methyl-4-fluoro-5-methoxyaniline 

Downstream Products

• 397-66-0 4-((Z)-3-fluoro-4-methoxy-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 717-79-3 3-amino-3-(3-fluoro-4-methoxy-phenyl)-propionic acid 
• 147906-08-9 (E)-3-(3-fluoro-4-methoxyphenyl)acrylic acid 
• 415949-83-6 methyl 2-(2-hydroxyphenyl)-2-(2-methoxy-5-methylphenyl)acetate 
• 415949-82-5 methyl 2-[2-benzyloxy-3-bromophenyl]-2-(2-methoxy-5-methylphenyl)acetate 
• 2070-43-1 2-fluoro-4-methyl-6-nitrophenol 
• 403-20-3 3-fluoro-p-anisic acid 
• 351-54-2 3-fluoro-p-anisaldehyde 
• 331-61-3 3-fluoro-4-methoxybenzyl bromide 

Relevant articles and documents

Fluorination of 4-alkyl-substituted phenols and aromatic ethers with fluoroxy and N-F reagents: Cesium fluoroxysulfate and N-fluoro-1,4-diazonia- bicyclo[2.2.2]octane dication salts case Dedicated to Prof. Dr. Boris ?emva in honor to his great contribution to fluorine chemistry.

4-Alkyl-substituted phenols and aromatic ethers were comparatively fluorinated with electrophilic fluorinating reagents such as cesium fluoroxysulfate (CFS), Selectfluor F-TEDA-BF4, and Accufluor NFTh in MeCN or MeOH. Reactions resulted in the formation of three types of products: 2-fluoro-4-alkyl-substituted corresponding compounds (5) as a result of ortho fluorination process, 4-alkyl-4-fluoro-cyclohexa-2,5- dienone compounds (6), resulting after an addition-elimination process, and 4-fluorosubstituted corresponding compounds (7) derived from ipso attack and release of the 4-alkyl group. The distribution of products depends on the bulkiness of alkyl groups at both positions and reaction media. The reaction in methanol proved more selective toward the formation of 2-fluoro derivatives. Tyramin and l-tyrozine were transformed with NFTh reagent in methanol to their fluorophenyl-substituted derivatives in good yield.

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

Reactions of N-fluorobenzenesulfonimide with methylbenzenes, phenols, and phenol ethers were studied under solvent-free conditions. The rate constant ratio for the reactions with mesitylene and durene indicates polar mechanism of the process. Solvent-free fluorination of aromatic compounds with N-fluorobenzenesulfonimide in some cases is more selective than reactions with other N-F reagents in a solvent.

First application of ionic liquids in electrophilic fluorination of arenes; Selectfluor (F-TEDA-BF4) for "green" fluorination

The NF fluorinating agent F-TEDA-BF4 dication salt (Selectfluor) 1 dissolves in imidazolium-based ionic liquids [emim][OTf] 7, [emim][BF4] 8, [bmim][PF6] 9 and [bmim][BF4] 10 (assisted by sonication), providing a convenient medium for fluorination of arenes under essentially acid-free conditions in a simple set-up (no volatile solvent; simple extraction of the aromatics without aqueous work-up), from which the ionic liquid can be easily recycled and reused. Comparative studies in [emim][OTf] 7 with anisole as substrate show that 1 is superior to NFTh-BF4 (Accufluor) 2 and that the N-fluoropyridinium salt NFPy-B2F7 4 is least effective. The scope of the reaction has been surveyed. Substrate selectivity (k mesitylene: k durene = 10) measured in competitive experiments in 7 is clearly indicative of a conventional polar mechanism. Substrate selectivity measured without the ionic liquid in MeCN solvent is also indicative of a polar mechanism but exhibits lower magnitude (k mesitylene: kdurene = 6). Addition of dicyclohexano-24-crown-8 to the fluorination reaction mixture (1 and anisole) in 7 reduced the conversion but did not change the isomer distribution. AM1 minimization was used to model the complexation of 1 with this crown. With reactive aromatics optimal fluorination yields in ionic liquids (using 1 equivalent of the NF reagent) are around 50% (higher for naphthalene). A key control experiment suggests that the free base (produced upon transfer-fluorination) could complex to unreacted 1 (generating a bulky dimer complex which may be ineffective for fluorine transfer) in competition to N-protonation.