24654-55-5 | 4-Fluorocinnamaldehyde

CAS:24654-55-5 | 4-Fluorocinnamaldehyde,Description

4-Fluorocinnamaldehyde, also known as (E)-3-(4-Fluorophenyl)-2-propenal, is a reagent used in the preparation of novel terminal bipheny-based diapophytoene desaturases which are used in the treatment of Staphylococcus aureus infections.

Molecular Structure Analysis

The molecular formula of 4-Fluorocinnamaldehyde is C9H7FO, with a molecular weight of 150.15. It is a fluorinated organic compound that belongs to the class of aldehydes.

Chemical Reactions Analysis

4-Fluorocinnamaldehyde has been used in the development of chemosensor probes. These probes are colorimetric sensors for naked-eye detection of AcO−/CN−/F− anions.

Physical And Chemical Properties Analysis

4-Fluorocinnamaldehyde is a liquid at 20°C. It has a density of 1.146 g/mL at 25°C and a refractive index of 1.599. It is air sensitive and heat sensitive.

Scientific Research Applications

Stereoconvergent Formylation

• Application : A study by Zemmouri et al. (2011) demonstrated the stereoconvergent formylation of β-bromo-β-fluorostyrene mixtures, leading to the synthesis of (Z)-α-fluorocinnamaldehydes. This process was optimized to yield good results and was extended to various styrenes. The resulting α-fluoroaldehydes were successfully reduced to (Z)-β-fluorocinnamic alcohol, which is a strong inhibitor of lignin polymerization (Zemmouri et al., 2011).

Synthesis in Microporous Polyaminals

• Application : Li, Zhang, and Wang (2016) utilized 4-fluorobenzaldehyde in the synthesis of microporous polyaminal networks. These fluorinated polymers showed increased surface areas and effective pore size tailoring, contributing to high CO2 adsorption capabilities. This is significant in environmental applications for CO2 capture and separation (Li, Zhang, & Wang, 2016).

Esterification in Medicinal Material Synthesis

• Application : Si (2004) reported the synthesis of methyl 4-fluorocinnamate, using 4-fluorocinnamic acid in esterification. This compound is significant in asymmetric dihydroxylation and aminohydroxylation, playing a vital role in the large-scale preparation of chiral medicinal materials (Si, 2004).

HPLC-Fluorescence Determination

• Application : Gatti et al. (1997) explored the use of 2-chloro-6,7-dimethoxy-3-quinolinecarboxaldehyde as a fluorogenic labeling agent in HPLC for chlorophenols. This process is relevant for pharmaceutical analysis, demonstrating the utility of fluorinated compounds in analytical chemistry (Gatti, Roveri, Bonazzi, & Cavrini, 1997).

Reductive Etherification in Radiopharmaceuticals

• Application : Funke et al. (2006) described the use of 4-[18F]fluoro-benzaldehyde for reductive etherification, producing various 4-[18F]fluorobenzyl ethers. This process is crucial in synthesizing radiopharmaceuticals, which are important in medical imaging and diagnostics (Funke, Jia, Fischer, Scheunemann, & Steinbach, 2006) .

Synthesis of Bifunctional Linkers

• Application : Crosby, Pietersz, and Ripper (2008) synthesized a series of 4-substituted benzaldehydes, including fluoro variants, as potential bifunctional linkers for drug-antibody conjugation in cancer therapy. These linkers varied in their para functionality, offering a range of potential acid labilities for therapeutic use (Crosby, Pietersz, & Ripper, 2008).

Safety And Hazards

4-Fluorocinnamaldehyde is combustible and can cause skin and eye irritation. It is recommended to wear protective gloves, eye protection, and face protection when handling it. In case of contact with eyes, rinse cautiously with water for several minutes.

More Information