452-81-3

Basic information

• Product Name: 2-FLUORO-4-METHYLPHENOL
• Synonyms: 2-Fluoro-p-cresol;2-FLUORO-4-METHYLPHENOL;3-Fluoro-4-hydroxytoluene, 2-Fluoro-p-cresol
• CAS NO: 452-81-3
• Molecular Formula: C₇H₇FO
• Molecular Weight: 126.13
• Product Categories: Aromatic Phenols;Miscellaneous
• Mol File: 452-81-3.mol

Chemical Properties

• Boiling Point: 173°Cat760mmHg
• Flash Point: 66.4°C
• Appearance: /
• Density: 1.164g/cm³
• Vapor Pressure: 0.967mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.01±0.18(Predicted)
• CAS DataBase Reference: 2-FLUORO-4-METHYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORO-4-METHYLPHENOL(452-81-3)
• EPA Substance Registry System: 2-FLUORO-4-METHYLPHENOL(452-81-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-34-22
• Safety Statements: 26-36/37/39
• RIDADR: 2922
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 452-81-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Fluoro-4-methylphenol is used as a building block in the field of organic synthesis for creating more complex molecules. Its phenolic structure and reactivity make it a valuable component in the synthesis of various organic compounds.
Used in Chemical Research:
In the realm of chemical research, 2-Fluoro-4-methylphenol is employed as a reference compound to study the effects of fluorination on the properties and reactivity of phenolic compounds. This helps in understanding the behavior of fluorinated molecules in different chemical reactions and their potential applications in various industries.
Used in Pharmaceutical Industry:
2-Fluoro-4-methylphenol is used as an intermediate in the synthesis of pharmaceutical compounds, particularly in the development of new drugs. Its unique structure and properties can contribute to the discovery of novel therapeutic agents with improved efficacy and safety profiles.
Used in Material Science:
In material science, 2-Fluoro-4-methylphenol is utilized in the development of new materials with specific properties, such as enhanced stability, reactivity, or selectivity. Its incorporation into polymers or other materials can lead to the creation of advanced materials with potential applications in various industries, including electronics, coatings, and adhesives.

InChI:InChI=1/C7H7FO/c1-5-2-3-7(9)6(8)4-5/h2-4,9H,1H3

Upstream product

• 452-80-2 2-fluoro-4-methylaniline 
• 106-44-5 p-cresol 
• 446-34-4 2-fluoro-4-methyl-1-nitrobenzene 
• 4783-71-5 2-(4-methylphenoxy)pyridine 
• 170981-26-7 2-fluoro-4-methylphenylboronic acid 

Downstream Products

• 2070-43-1 2-fluoro-4-methyl-6-nitrophenol 
• 2967-69-3 (2-fluoro-4-methyl-phenoxy)-acetic acid 
• 32862-24-1 C₁₄H₁₂FNO₄ 
• 32862-25-2 C₁₅H₁₄FNO₄ 
• 1443342-79-7 C₁₃H₁₇FO₃ 
• 765302-76-9 C₁₃H₁₀BrFO 
• 1072003-84-9 tert-butyl [5-(2-fluoro-4-methylphenoxy)-2-nitrophenyl]methylcarbamate 
• 1416976-44-7 C₁₀H₁₁FO₃ 
• 1427406-95-8 2-fluoro-6-methyl-3-triisopropylsilyloxy-benzoic acid 
• 1427406-96-9 1,3-bis(2-fluoro-6-methyl-3-triisopropylsilyloxyphenyl)urea 
• 1427406-94-7 (2-fluoro-4-methylphenoxy)triisopropyl-silane 
• 2138-22-9 4-chloro-1,2-benzenediol 
• 645405-05-6 C₆H₄ClFO₂ 

Relevant articles and documents

Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward “Dry” Processes

An effective protocol for the solvent-free fluorination of electron-rich aromatic compounds with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) is described. The protocol allows the easy and efficie

Coordination Polymers as a Functional Material for the Selective Molecular Recognition of Nitroaromatics and ipso-Hydroxylation of Arylboronic Acids

We report the synthesis and structural characterization of two coordination polymers (CPs), namely; [{Zn(L)(DMF)4} ? 2BF4]α (1) and [{Cd(L)2(Cl)2} ? 2H2O]α (2) (where L=N2,N6-di(pyridin-4-yl)naphthalene-2,6-dicarboxamide). Crystal packing of 1 reveals the existence of channels running along the b- and c-axis filled by the ligated DMF and lattice anions, respectively. Whereas, crystal packing of 2 reveals that the metallacycles of each 1D chain are intercalating into the groove of adjacent metallacycles resulting in the stacking of 1D loop-chains to form a sheet-like architecture. In addition, both 1 and 2 were exploited as multifunctional materials for the detection of nitroaromatic compounds (NACs) as well as a catalyst in the ipso-hydroxylation of aryl/heteroarylboronic acids. Remarkably, 1 and 2 showed high fluorescence stability in an aqueous medium and displayed a maximum 88% and 97% quenching efficiency for 4-NPH, respectively among all the investigated NACs. The mechanistic investigation of NACs recognition suggested that the fluorescence quenching occurred via electron as well as energy transfer process. Furthermore, the ipso-hydroxylation of aryl/heteroarylboronic acids in presence of 1 and 2 gave up to 99% desired product yield within 15 min in our established protocol. In both cases, 1 and 2 are recyclable upto five cycles without any significant loss in their efficiency.

Synthesis of 2 - fluoro phenol compounds

The present invention provides a method for synthetizing a 2-fluoro phenol compound shown in a formula IV. The phenol compound shown in the formula I is prepared into a 2-pyridine oxygroup arene compound shown in a formula II through an Ullmann reaction, the 2-pyridine oxygroup arene compound shown in the formula II is mixed with a palladium catalyst, a fluorinating reagent, an additive and an organic solvent, the mixture is stirred under the temperature of 30-160 DEG C to perform a fluorination reaction to obtain an ortho-position fluoridated 2-pyridine oxygroup arene compound shown in a formula III, and the ortho-position fluoridated 2-pyridine oxygroup arene compound shown in the formula III is prepared into the 2-fluoro phenol compound shown in the formula IV through the action of alkali. The method provided by the present invention has the advantages of mild reaction conditions, simplicity in operations, good substrate adaptability, high fluorination selectivity and the like. The 2-fluoro phenol compound is shown in the figure below.

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.

Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media

The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.

The role of F-N reagent and reaction conditions on fluoro functionalisation of substituted phenols

The effect of steric interactions on the regioselectivity of fluorination of para alkyl substituted phenols was investigated and the strong effect of size of the alkyl substituent, the structure of the F-N reagent and the solvent on the site of fluorination was established. The course of reaction obeyed a second order rate equation, while the fluorination process required higher ΔH≠ activation than oxidation or oxidative demethylation. Solvent polarity variations had a small effect on the rate of functionalisation, while an excellent Hammett correlation with ρ+=-2.3 was determined.

DIRECT FLUORINATION OF PHENOL AND CRESOLS

A study has been made of the reaction of phenol with elemental fluorine using a variety of solvents and reaction temperatures.Yields of o- and p-fluorophenol were obtained as high as 85percent.The isomer ratio changed drastically between phenol conversions of 10percent and 56percent.The o-isomer changed to unidentified polymeric substances at higher conversion, but it might also be assumed that interconversion of some isomers is occuring.The three cresols have also been succesfully fluorinated with elemental fluorine. p-Cresol gave some expected 2-fluoroderivative but also formed a fluorocyclohexadienyl ketone.