367-12-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluorophenol is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure, which includes a fluorine atom, makes it a valuable building block for the development of new drugs with improved properties, such as enhanced bioavailability and metabolic stability.
Used in Chemical Synthesis:
In the chemical industry, 2-Fluorophenol is utilized as a starting material for the production of various organic compounds, including agrochemicals, dyes, and specialty chemicals. The presence of the fluorine atom in its structure allows for the creation of a wide range of derivatives with diverse applications.
Used in Material Science:
2-Fluorophenol can be employed in the development of advanced materials, such as polymers and coatings, due to its unique chemical and physical properties. The incorporation of fluorine into the phenol structure can lead to materials with improved thermal stability, chemical resistance, and non-stick properties.
Used in Research and Development:
As a versatile and reactive compound, 2-Fluorophenol is often used in research and development settings to explore new chemical reactions and synthetic pathways. Its reactivity and unique properties make it an attractive candidate for the development of novel compounds and materials with potential applications in various industries.

Synthesis Reference(s)

Tetrahedron, 52, p. 23, 1996 DOI: 10.1016/0040-4020(95)00867-8Journal of the American Chemical Society, 103, p. 1964, 1981 DOI: 10.1021/ja00398a015

Air & Water Reactions

Highly flammable.

Reactivity Profile

2-Fluorophenol reacts as a weak organic acid. May be incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction with bases. Such heating may initiate polymerization of the organic compound. Sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Nitrated very rapidly, even by dilute nitric acid.

Health Hazard

ACUTE/CHRONIC HAZARDS: Toxic and irritant.

Purification Methods

Pass o-fluorophenol at least twice through a gas chromatographic column for small quantities; otherwise fractionally distil it under reduced pressure. [Beilstein 6 I 97, 6 IV 770.]

InChI:InChI=1/C6H5FO/c7-5-3-1-2-4-6(5)8/h1-4,8H

Upstream product

• 321-28-8 1-fluoro-2-methoxybenzene 
• 451-80-9 1-ethoxy-2-fluoro-benzene 
• 108-24-7 acetic anhydride 
• 95-55-6 2-amino-phenol 
• 462-06-6 fluorobenzene 
• 87804-23-7 2-(1-hydroxyethyl)phenol 
• 348-51-6 1-chloro-2-fluorobenzene 
• 40473-50-5 2-(hydroxy(phenyl)methyl)phenol 
• 1529-17-5 phenyltrimethylsilyl ether 
• 90-01-7 salicylic alcohol 
• 90-03-9 (2-hydroxyphenyl)mercury chloride 
• 108-95-2 phenol 
• 40161-40-8 2-fluoro-1-(diethoxymethylsilyl)benzene 
• 29650-44-0 2-fluorophenyl acetate 

Downstream Products

• 349-21-3 1-(2-fluoro-phenoxy)-4-methoxy-benzene 
• 2263-18-5 (2-fluoro-phenyl)-octyl ether 
• 394-50-3 3-fluorosalicylaldehyde 
• 405-05-0 3-fluoro-4-hydroxybenzaldehyde 
• 326-57-8 1,3-bis-(2-fluoro-phenoxy)-propan-2-ol 
• 370-74-1 (2-fluoro-phenyl)-(4-nitro-benzyl)-ether 
• 349-40-6 (2-fluoro-phenyl)-(4-methyl-benzyl)-ether 
• 348-10-7 (2-fluorophenoxy)acetic acid 
• 451-06-9 chloro-acetic acid-(2-fluoro-phenyl ester) 
• 399-28-0 rac-3-(2-fluorophenoxy)propane-1,2-diol 
• 347-70-6 isovaleric acid-(2-fluoro-phenyl ester) 
• 2795-61-1 2-(2-fluoro-phenoxy)-benzoic acid 
• 67587-28-4 13-(2-Fluoro-phenoxy)-12-hydroxy-8-(1-hydroxy-ethyl)-tridecanoic acid 
• 67587-36-4 7-{[5-(2-Fluoro-phenoxy)-4-hydroxy-pentyl]-methanesulfonyl-amino}-heptanoic acid ethyl ester 

Relevant academic research and scientific papers

AROMATIC FLUORINE CHEMISTRY. PART 3. PREPARATION OF FLUOROPHENOLS VIA HYDROLYSIS OF CHLOROFLUOROBENZENES

The 1,2-, 1,3-, and 1,4-fluorophenols have been prepared by a copper (e.g.CuO, CuSO4) catalyzed hydrolysis of chlorofluorobenzenes under conditions of controlled pH.

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Method for preparing O-fluorophenol by one-pot method

The invention discloses a method for preparing o-fluorophenol by a one-pot method, and belongs to the technical field of organic synthesis. O-bromine/chlorofluorobenzene is used as a raw material, a 2-fluorophenyl Grignard reagent is obtained through magnesium metal or Grignard reagent exchange in the presence of a stabilizer, and then oxygen or compressed air is introduced to obtain the o-fluorophenol. The method is simple and convenient in reaction operation, less in three wastes, high in yield and free of isomers, inhibits elimination of a Grignard reagent due to addition of the stabilizer, and accords with industrial amplification prospects.

Synthesis method of fluorine-containing phenol structure compound

The invention discloses a synthesis method of a fluorine-containing phenol structure compound, and belongs to the technical field of chemical synthesis. Fluorine-containing benzoic acid is subjected to a one-pot reaction in a solvent under the action of alkali to obtain fluorine-containing phenate, and fluorine-containing phenol is obtained after acid regulation and dissociation. The synthesis method has the advantages of rich, cheap and easily available raw material structure, short synthesis steps, mild reaction conditions, simple and convenient operation, high synthesis yield, good productquality, wide application range and the like, and is suitable for simple and efficient synthesis of various high-value and high-purity fluorine-containing phenol compounds.

Preparation method of 2-fluorophenol

The invention relates to the field of fluorine-containing compounds, and particularly discloses a preparation method of 2-fluorophenol. The invention relates to a preparation method of 2-fluorophenol.The preparation method comprises the following steps: (1) diazotization reaction: adding 2-fluoroaniline into a dilute acid solution under stirring, cooling after the reaction is finished, dropwise adding a sodium nitrite water solution, stirring, and keeping the temperature to obtain a diazonium salt solution; (2) quenching: adding urea into the diazonium salt solution, and stirring to obtain anintermediate solution; (3) hydrolysis reaction: firstly, mixing a copper salt aqueous solution with an organic solvent to obtain a mixed solution, dropwise adding the intermediate solution into the preheated mixed solution, and obtaining a hydrolysate after dropwise adding is finished; wherein the organic solvent is immiscible with water; and (4) post-treatment: carrying out post-treatment on thehydrolysate to obtain 2-fluorophenol. The preparation method has the advantages that the yield and purity of 2-fluorophenol are high, the use amount of a copper catalyst is reduced, and hydrolysis side reactions are reduced.

Phenol compound ortho-position direct fluorination method

The invention relates to a phenol compound ortho-position direct fluorination method which comprises the following steps: reacting a phenol compound shown in a formula (1A) with a fluorination reagentin a solvent under the action of a photocatalyst and a light source at room temperature, and separating and purifying a reaction mixture after the reaction to obtain a fluorinated phenol compound shown in a formula (2A). The advantages are as follows: the method for directly fluorinating phenol by organic photocatalysis is simple in operation process; raw materials are commercialized and easy toobtain; the photocatalyst is low in price, easy to obtain and environmentally friendly; the reaction condition is mild; the site selectivity is high; the reaction is efficient; and a fluorinated phenol derivative can be prepared only through one step.

The highly efficient air oxidation of aryl and alkyl boronic acids by a microwave-assisted protocol under transition metal-free conditions

Molecular oxygen is the most important green-oxidant due to its excellent properties. However, the effective utilization of molecular oxygen remains a major challenge in modern chemistry. Herein, we report the development a rapid, green and efficient microwave-assisted protocol for the air oxidation of boronic acids to phenols and alcohols under transition metal-free conditions. In the presence of KOH and DMSO, high yields of the expected phenols and alcohol were obtained with microwave-assistance, and a variety of functional groups were tolerated in this procedure. Notably, this transition metal-free method represents a breakthrough in both organic synthesis and green chemistry for the oxidative hydroxylation of boronic acids to phenols and alcohols.

Phthalocyanine Zinc-catalyzed Hydroxylation of Aryl Boronic Acids under Visible Light

A visible-light-promoted aerobic oxidative hydroxylation of boronic acids using phthalocyanine zinc as an easily available photosensitizer has been developed. It provided a direct access to synthesize aliphatic alcohols and phenols from boronic acids. The advantages of this approach included the low catalyst loading (0.5 mol%), high efficient, the use of O2 as an oxygen source, wide substrate range, the simple operational process, and mild conditions. (Figure presented.).

Room-Temperature Ionic Liquids (RTILs) as Green Media for Metal- and Base-Free ipso -Hydroxylation of Arylboronic Acids

The oxidative hydroxylation of arylboronic acids to the corresponding phenolic compounds under metal- and base-free aerobic conditions is successfully demonstrated on a greener media. Hydrogen peroxide, as an eco-friendly oxidant, is compatible with green mediates room-temperature ionic liquids (RTIL)s, providing hydroxylation products of arylboronic acids in an efficient manner. The RTIL support is particularly interesting for its reusability.