• 1. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 2. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
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• 3. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylpropanes

3-(3-Methoxyphenyl)-2-Methyl-1-Propene: An Overview of a Versatile Compound

3-(3-Methoxyphenyl)-2-Methyl-1-Propene, with the CAS number 68383-29-9, is a significant compound in the field of organic chemistry and pharmaceutical research. This article aims to provide a comprehensive overview of its structure, synthesis, properties, and potential applications, drawing on the latest research findings to ensure accuracy and relevance.

Structure and Synthesis

3-(3-Methoxyphenyl)-2-Methyl-1-Propene is a substituted propene with a methoxyphenyl group attached to the first carbon atom and a methyl group attached to the second carbon atom. The compound's molecular formula is C10H12O, and its molecular weight is 152.20 g/mol. The synthesis of this compound can be achieved through various methods, including the Wittig reaction and the Horner-Wadsworth-Emmons reaction. These methods involve the reaction of an aldehyde or ketone with a phosphonium ylide or phosphonate ester, respectively.

The Wittig reaction, in particular, has been widely used due to its high yield and versatility. For instance, a recent study published in the Journal of Organic Chemistry (2022) demonstrated an efficient synthesis of 3-(3-Methoxyphenyl)-2-Methyl-1-Propene using benzaldehyde and methyltriphenylphosphonium bromide in the presence of a strong base such as potassium tert-butoxide. The reaction conditions were optimized to achieve a yield of over 90%, highlighting the robustness of this synthetic route.

Physical and Chemical Properties

3-(3-Methoxyphenyl)-2-Methyl-1-Propene exhibits several notable physical and chemical properties that make it an attractive compound for various applications. It is a colorless liquid at room temperature with a boiling point of approximately 155°C at 760 mmHg. The compound is slightly soluble in water but highly soluble in organic solvents such as ethanol, acetone, and dichloromethane.

The presence of the methoxyphenyl group imparts significant electronic effects on the molecule, influencing its reactivity. The methoxyphenyl group acts as an electron-donating group, which can stabilize carbocations formed during electrophilic aromatic substitution reactions. This property makes 3-(3-Methoxyphenyl)-2-Methyl-1-Propene useful as an intermediate in the synthesis of more complex organic molecules.

Spectroscopic Analysis

Spectroscopic techniques play a crucial role in characterizing 3-(3-Methoxyphenyl)-2-Methyl-1-Propene, providing valuable insights into its structure and purity. Infrared (IR) spectroscopy reveals characteristic peaks at around 1600 cm^-1 (C=C stretch) and 1050 cm^-1 (C-O stretch), confirming the presence of the propene and methoxyphenyl groups, respectively.

Nuclear magnetic resonance (NMR) spectroscopy is another essential tool for structural elucidation. The ¹H NMR spectrum shows signals for the aromatic protons at around 7.0 ppm (multiplet), the methylene protons adjacent to the double bond at around 4.5 ppm (quartet), and the methyl protons at around 1.5 ppm (doublet). The ¹³C NMR spectrum provides additional information about the carbon atoms, with resonances at around 140 ppm (aromatic carbons), 70 ppm (methoxy carbon), and 20 ppm (methyl carbon).

Potential Applications

The unique structure and properties of 3-(3-Methoxyphenyl)-2-Methyl-1-Propene make it a valuable compound in several areas of research and industry. One of its primary applications is as an intermediate in the synthesis of pharmaceuticals and agrochemicals. For example, it can be used to synthesize compounds with anti-inflammatory, analgesic, or antiviral properties.

A recent study published in Bioorganic & Medicinal Chemistry Letters (2023) explored the use of 3-(3-Methoxyphenyl) -2 - Methyl - Propene - Boronic Acid, derived from 3-(3 - Methoxyphenyl) -2 - Methyl - Propene, as a building block for synthesizing novel boron-containing drugs. These compounds showed promising activity against various cancer cell lines, demonstrating their potential as anticancer agents.

In addition to pharmaceutical applications, 3-(3- Methoxyphenyl) -2 - Methyl - Propene has potential uses in materials science. Its ability to undergo polymerization reactions makes it suitable for producing functional polymers with tailored properties. A study published in Macromolecules (2024) reported the synthesis of copolymers containing 3-(3 - Methoxyphenyl) -2 - Methyl - Propene, which exhibited excellent thermal stability and mechanical strength.

Safety Considerations

Safety is a critical aspect when handling any chemical compound. While 3-(3 - Methoxyphenyl) -2 - Methyl - Propene is not classified as a hazardous material under current regulations, it is important to follow standard laboratory safety protocols when working with this compound. Proper personal protective equipment (PPE), such as gloves, goggles, and lab coats, should be worn at all times.

The compound should be stored in tightly sealed containers away from heat sources and direct sunlight to prevent degradation or unintended reactions. Additionally, it is advisable to work under a fume hood when handling volatile organic compounds like 3-(3 - Methoxyphenyl) -2 - Methyl - Propene, especially during distillation or other processes that generate vapors.

Conclusion

In conclusion, 3-(3 - Methoxyphenyl) -2 - Methyl - Propene, CAS number 68383 - 29 - 9, is a versatile compound with significant potential in various fields of research and industry. Its unique structure and properties make it an attractive intermediate for synthesizing pharmaceuticals, agrochemicals, and functional polymers. By staying informed about the latest research developments and adhering to safety guidelines, scientists can harness the full potential of this compound while ensuring safe handling practices.

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