214822-96-5 | METHYL 4-FLUORO-3-HYDROXYBENZOATE

CAS:214822-96-5 | METHYL 4-FLUORO-3-HYDROXYBENZOATE,Description

Methyl 4-Fluoro-3-hydroxybenzoate is a chemical compound with the molecular formula C8H7FO3. It is commonly used in the synthesis of trisubstituted imidazole derivatives containing a 4-fluorophenyl group, a pyrimidine ring, and a CN- or CONH2-substituted benzyl moiety.

Synthesis Analysis

The synthesis of Methyl 4-Fluoro-3-hydroxybenzoate involves several steps. The compound is synthesized from the reaction of Methyl 4-fluorobenzoate with other reagents.

Molecular Structure Analysis

The molecular structure of Methyl 4-Fluoro-3-hydroxybenzoate consists of a benzene ring substituted with a fluorine atom, a hydroxyl group, and a methyl ester group. The average molecular mass is 170.138 Da.

Chemical Reactions Analysis

Methyl 4-Fluoro-3-hydroxybenzoate can participate in various chemical reactions. For instance, it can be used in the synthesis of trisubstituted imidazole derivatives.

Physical And Chemical Properties Analysis

Methyl 4-Fluoro-3-hydroxybenzoate is a solid at room temperature. It has a melting point range of 90.0 to 94.0 °C. The compound is soluble in methanol.

Scientific Research Applications

Crystal Structure and Theoretical Analysis

Methyl 4-hydroxybenzoate, known as methyl paraben, serves as an antimicrobial agent in various products. A study detailed the crystal structure of this compound, revealing a 3D framework formed through extensive intermolecular hydrogen bonding. The study combined experimental and computational approaches, including Hirshfeld surface analysis and quantum mechanical methods, to analyze the molecule's structure and interactions. This research provides insights into the compound's stability and reactivity, which are crucial for its applications in the pharmaceutical and cosmetic industries (Sharfalddin et al., 2020).

Fluorescent Sensing Applications

Methyl 4-Fluoro-3-hydroxybenzoate derivatives have been explored for their potential in sensing applications. A study reported the synthesis of a fluorogenic chemosensor based on this compound, demonstrating high selectivity and sensitivity towards Al³⁺ ions. This sensor showed a promising application in bio-imaging, specifically for detecting Al³⁺ in human cervical HeLa cancer cell lines, highlighting its potential utility in medical diagnostics and research (Ye et al., 2014).

Environmental and Microbial Studies

Research has also investigated the environmental and microbial interactions of fluorinated derivatives of Methyl 4-Fluoro-3-hydroxybenzoate. One study used fluorinated compounds to track the metabolic degradation pathways of m-Cresol in a methanogenic consortium, shedding light on the complex processes of microbial degradation. This research contributes to our understanding of environmental biodegradation and the potential impacts of fluorinated compounds on microbial ecosystems (Londry & Fedorak, 1993).

Enzymatic Studies

Enzymatic reactions involving Methyl 4-Fluoro-3-hydroxybenzoate have been studied to understand their biological transformations. A particular focus has been on 3-Hydroxybenzoate 4-hydroxylase from Pseudomonas testosteroni, which catalyzes the hydroxylation of 3-hydroxybenzoate to protocatechuate. This research provides valuable insights into the enzyme's substrate specificity and reaction mechanisms, which are relevant for biotechnological applications and the synthesis of complex organic compounds (Michalover et al., 1973).

Safety And Hazards

Methyl 4-Fluoro-3-hydroxybenzoate is classified as a potentially hazardous substance. It can cause skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Precautionary measures include avoiding dust formation, avoiding contact with skin, eyes, or clothing, and ensuring adequate ventilation.

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