4-Fluoro-3-hydroxybenzoic acid
[CAS# 51446-31-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 4-Fluoro-3-hydroxybenzoic acid
• Molecular Formula: C₇H₅FO₃
• Molecular Weight: 156.11
• CAS Registry Number: 51446-31-2
• EC Number: 625-872-5
• SMILES: C1=CC(=C(C=C1C(=O)O)O)F

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 214-218 °C (expl.)
• Index of Refraction: 1.585, Calc.^*
• Boiling Point: 324.0±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 149.7±23.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Fluoro-3-hydroxybenzoic acid is an organic compound that consists of a benzene ring with both a hydroxyl group (-OH) and a fluoro group (-F) attached to the ring. It is a derivative of benzoic acid and is commonly used in organic synthesis and various chemical applications. The compound has a distinct structure, with the hydroxy group positioned at the 3-position and the fluoro group at the 4-position on the benzene ring.

The synthesis and applications of 4-fluoro-3-hydroxybenzoic acid are well-established in the chemical literature. Its synthesis typically involves fluorination of 3-hydroxybenzoic acid, which can be achieved using a variety of methods. These methods include electrophilic aromatic substitution reactions, where a fluorinating agent such as hydrogen fluoride (HF) or a fluorine source like a fluorine gas or fluorine-containing reagents is used to introduce the fluorine atom to the aromatic ring. The hydroxy group is a directing group, which facilitates the substitution at the para-position (4-position) relative to the hydroxyl group.

The compound is primarily used as a building block in the synthesis of more complex molecules. It serves as a versatile intermediate for the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. One of the main areas of application is in the production of drugs, where the presence of both a fluorine atom and a hydroxyl group in the aromatic structure can impart specific bioactive properties. Fluorine substitution is known to enhance the stability and bioavailability of certain drug molecules, making 4-fluoro-3-hydroxybenzoic acid an important compound in medicinal chemistry.

In addition to its use in pharmaceuticals, 4-fluoro-3-hydroxybenzoic acid is also employed in the synthesis of various agrochemicals. The introduction of fluorine into an aromatic ring can significantly alter the chemical and biological properties of the molecule, and this can be beneficial for the development of herbicides, insecticides, and fungicides. The compound’s ability to modify the electronic properties of the aromatic ring makes it a valuable intermediate for the design of more effective agrochemical agents.

The chemical compound is also of interest in the field of materials science. It has been used in the synthesis of polymers and materials with specific properties, such as increased thermal stability, hydrophobicity, or improved mechanical strength. The fluoro group is particularly useful in modifying the surface properties of materials, making them more resistant to environmental factors like moisture, oxidation, and extreme temperatures.

Furthermore, 4-fluoro-3-hydroxybenzoic acid is used in research as a precursor for the synthesis of other fluorinated aromatic compounds. Its chemical reactivity and the presence of both a hydroxyl group and a fluorine atom make it a useful intermediate for creating more complex molecular structures, particularly in the study of molecular interactions, catalysis, and surface chemistry.

Overall, 4-fluoro-3-hydroxybenzoic acid is an important chemical compound with diverse applications in organic synthesis, medicinal chemistry, agrochemical development, and materials science. Its ability to act as an intermediate for the production of a wide range of functionalized molecules makes it a key component in the development of novel and effective chemical agents.

References

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