2561-17-3 | 3-FLUOROPHENYLACETYLENE

CAS:2561-17-3 | 3-FLUOROPHENYLACETYLENE,Description

3-Fluorophenylacetylene is an organic compound with the molecular formula C8H5F. It is used as an intermediate in the synthesis of liquid crystals.

Synthesis Analysis

The synthesis of 3-Fluorophenylacetylene involves a multi-step reaction with two steps. The first step involves a reaction with magnesium in diethyl ether under heating conditions, yielding an 82% yield. The second step involves a reaction with butyllithium in diethyl ether, yielding an 84% yield.

Molecular Structure Analysis

The molecular structure of 3-Fluorophenylacetylene has been studied using various spectroscopic methods. The relative location of the fluorine atom with respect to the acetylenic group can influence the transition energy and molecular vibration.

Physical And Chemical Properties Analysis

3-Fluorophenylacetylene has a molecular weight of 120.12 g/mol. It has a density of 1.1±0.1 g/cm3, a boiling point of 148.7±23.0 °C at 760 mmHg, and a vapour pressure of 5.3±0.3 mmHg at 25°C.

Scientific Research Applications

Structural Analysis and Spectroscopy

3-Fluorophenylacetylene (3FPA) has been extensively studied for its structural and spectroscopic properties. Jang et al. (2016) explored its microwave spectrum, structure, and dipole moment using chirped-pulse Fourier-transform microwave (CP-FTMW) spectroscopy, contributing to a deeper understanding of its molecular geometry and electronic properties (Jang et al., 2016).

Interaction with Water

The interaction of water with fluorophenylacetylenes, including 3FPA, was investigated by Maity and Patwari (2009). They focused on hydrogen bonding and its impact on molecular behavior, revealing insights into the chemical nature of these interactions (Maity & Patwari, 2009).

Synthesis of Complex Compounds

In the realm of synthetic chemistry, 3FPA serves as a key intermediate. Ragaini et al. (2009) demonstrated its use in the synthesis of indoles, crucial for creating pharmaceutical compounds like Fluvastatin (Ragaini et al., 2009).

Crystallography and Polymorphism

Dikundwar et al. (2011) studied the crystal structures of 3FPA, highlighting its polymorphism and the various crystal forms it can adopt. Such studies are pivotal in materials science and pharmaceutical formulation (Dikundwar et al., 2011).

Fluorescent Sensing

The chemical properties of 3FPA make it suitable for developing fluorescent sensors. Thanayupong et al. (2017) created a turn-on fluorescent sensor for cyanide detection based on a phenylacetylene derivative, demonstrating its potential in environmental monitoring (Thanayupong et al., 2017).

π-Stacking and Molecular Interactions

Kundu et al. (2020) focused on the π-stacking of hetero-dimers of fluorophenylacetylenes, including 3FPA. Their research provides valuable insights into the molecular interactions and stability of such compounds, which is vital for designing new materials and drugs (Kundu et al., 2020) .

Scientific Research Applications of 3-Fluorophenylacetylene

Spectroscopic Properties and Structure Analysis

• Microwave Spectrum and Molecular Structure : Jang et al. (2016) analyzed the microwave spectrum of 3-fluorophenylacetylene (3FPA), determining its rotational constants and dipole moment. This research aids in understanding its gas phase molecular structure, which is crucial for further chemical applications (Jang et al., 2016).
• Interactions with Water : Studies by Maity and Patwari (2009) on the water complexes of fluorophenylacetylenes, including 3FPA, provide insights into their hydrogen bonding and interaction with water, which is significant in various chemical and biological contexts (Maity & Patwari, 2009).

Chemical Synthesis and Applications

• Synthesis of Indoles : Ragaini et al. (2009) demonstrated the use of arylalkynes like 3FPA in the palladium/phenanthroline-catalyzed synthesis of indoles, a key structural component in many pharmaceutical compounds (Ragaini et al., 2009).
• Crystal Structure and Polymorphism : Dikundwar et al. (2011) investigated the crystal structures of 3FPA, uncovering its ability to form different polymorphs. This knowledge is essential for the development of new materials and drugs (Dikundwar et al., 2011).

Safety And Hazards

3-Fluorophenylacetylene may cause respiratory irritation, serious eye irritation, and skin irritation. It is also a flammable liquid and vapour. Safety measures include avoiding dust formation, breathing mist, gas or vapours, and contact with skin and eyes. Use of personal protective equipment and chemical impermeable gloves is recommended.

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