2713-33-9 | 3,4-Difluorophenol

CAS:2713-33-9 | 3,4-Difluorophenol,Description

3,4-Difluorophenol is a chemical compound that is part of the broader class of difluorophenols. These compounds are characterized by having two fluorine atoms attached to a phenol ring. The specific placement of the fluorine atoms at the 3 and 4 positions of the aromatic ring distinguishes 3,4-difluorophenol from its isomers. The presence of fluorine atoms can significantly affect the chemical and physical properties of the compound, such as acidity, reactivity, and phase behavior.

Synthesis Analysis

The synthesis of compounds related to 3,4-difluorophenol can be achieved through various methods. For instance, the synthesis of 3,4-difluorothiophenol ester liquid crystal compounds has been reported with yields ranging from 64.2% to 74.9%. These compounds were characterized using IR and 1H NMR spectroscopy. Additionally, the synthesis of 3-polyfluoroacylmethylenephthalides, which are structurally related to difluorophenols, involves cyclodehydration of certain precursors, demonstrating the versatility of fluorinated compounds in synthetic chemistry.

Molecular Structure Analysis

The molecular structure of compounds closely related to 3,4-difluorophenol has been studied using various techniques. For example, the crystal and molecular structure of anti-3',4'-difluoro-2-hydroxyiminopropiophenone, which shares the difluorophenol moiety, was determined using X-ray diffraction. This analysis revealed a monoclinic space group and provided insights into the molecular conformation and intermolecular interactions.

Chemical Reactions Analysis

The reactivity of difluorophenols can be influenced by the presence of fluorine atoms. In a study on the regioexhaustive functionalization of difluorophenols, including 3,4-difluorophenol, it was shown that the phenolic hydrogen atom can be replaced by various groups, leading to a diverse array of hydroxybenzoic acids. This demonstrates the potential of 3,4-difluorophenol to undergo selective chemical transformations, which is a key aspect of diversity-oriented synthesis.

Physical and Chemical Properties Analysis

The physical and chemical properties of difluorophenol derivatives can be quite distinct. For instance, the thermal analysis of 3,4-difluorothiophenol ester compounds revealed that they possess a broad nematic phase range and high clearing points, indicating their potential application in liquid crystal technology. Moreover, the study of the crystalline and nematic phases of a trifluorophenyl compound provided insights into molecular packing and van der Waals interactions, which are also relevant for understanding the behavior of 3,4-difluorophenol derivatives.

Scientific Research Applications

Organic Chemistry

3,4-Difluorophenol is used as a starting reagent in the synthesis of various organic compounds.

Application

It’s used in the synthesis of 4,6-difluoro-5,7-dihydroxytryptamine and 3-carboxy-6,8-difluoro-7-hydroxycoumarin (Pacific Blue), a fluorinated fluorescent dye.

Results

Biochemistry

3,4-Difluorophenol has been studied for its transformation by Penicillium frequentans strain Bi 7/2.

Application

The fungus Penicillium frequentans can transform 3,4-Difluorophenol when using phenol as a sole source of carbon and energy.

Safety And Hazards

3,4-Difluorophenol is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is a flammable solid and is harmful if swallowed, in contact with skin, or if inhaled. It causes severe skin burns and eye damage.

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