Production Method 1

135049-82-0

1066-54-2

91142-24-4

Reaction Conditions

1.1 Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium Solvents: Triethylamine ;  12 h, 80 °C
1.2 Reagents: Potassium carbonate Solvents: Methanol ;  12 h, rt

Reference

Discovery of Novel Sphingosine-1-Phosphate-1 Receptor Agonists for the Treatment of Multiple Sclerosis

Park, Sun Jun; Yeon, Seul Ki; Kim, Yoowon; Kim, Hyeon Jeong; Kim, Siwon; et al, Journal of Medicinal Chemistry, 2022, 65(4), 3539-3562

Production Method 2

135049-82-0

1066-54-2

91142-24-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide ,  Tetrakis(triphenylphosphine)palladium Solvents: Triethylamine ;  rt → 80 °C; 4 h, 80 °C
1.2 Reagents: Potassium carbonate Solvents: Methanol ;  overnight, rt

Reference

Synthesis and Antiplasmodial Activity of New Indolone N-Oxide Derivatives

Nepveu, Francoise; Kim, Sothea; Boyer, Jeremie; Chatriant, Olivier; Ibrahim, Hany; et al, Journal of Medicinal Chemistry, 2010, 53(2), 699-714

Production Method 3

91142-24-4

Reaction Conditions

Reference

Halogen Bonding of (Iodoethynyl)benzene Derivatives in Solution

Dumele, Oliver; Wu, Dino; Trapp, Nils; Goroff, Nancy; Diederich, Francois, Organic Letters, 2014, 16(18), 4722-4725

Production Method 4

135049-82-0

1066-54-2

91142-24-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Triphenylphosphine ,  Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium Solvents: Triethylamine ;  overnight, rt
1.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  overnight, rt

Reference

Polymerization of ortho-Substituted Phenylacetylenes with Well-Defined Ruthenium-Alkylidene Catalysts and Related Metathesis Initiators

Katsumata, Toru; Shiotsuki, Masashi; Sanda, Fumio; Sauvage, Xavier; Delaude, Lionel; et al, Macromolecular Chemistry and Physics, 2009, 210(22), 1891-1902

Production Method 5

91142-24-4

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt → -78 °C
1.2 Reagents: Butyllithium Solvents: Hexane ;  15 min, -78 °C; 2 h, -78 °C → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  0 °C → rt

Reference

Investigating direct access to 2-oxaspiro[4.5]decanones via 6π-electrocyclization

Pouwer, Rebecca H.; Schill, Heiko; Williams, Craig M.; Bernhardt, Paul V., European Journal of Organic Chemistry, 2007, (28), 4699-4705

Production Method 6

877603-48-0

91142-24-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol ,  Dichloromethane

Reference

2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behavior and antiplasmodial activities

Najahi, Ennaji; Valentin, Alexis; Fabre, Paul-Louis; Reybier, Karine; Nepveu, Francoise, European Journal of Medicinal Chemistry, 2014, 78, 269-274

1-ethynyl-4-(propan-2-yloxy)benzene Raw materials

• Benzene, 1-(1-methylethoxy)-4-[2-(trimethylsilyl)ethynyl]-
• 1-Iodo-4-(propan-2-yloxy)benzene
• ethynyltrimethylsilane

1-ethynyl-4-(propan-2-yloxy)benzene Preparation Products

• 1-ethynyl-4-(propan-2-yloxy)benzene (91142-24-4)

• 1. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 2. Evolution of dealloying induced strain in nanoporous gold crystals?
  Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
• 3. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 4. Disulfide- and terminal alkyne-functionalized magnetic silica particles for enrichment of azido glycopeptides?
  Sheng Wang,Wenxian Xie,Xiu Zhang,Xia Zou,Yan Zhang Chem. Commun., 2012,48, 5907-5909
• 5. Excited state characterization of carbonyl containing carotenoids: a comparison between single and multireference descriptions?
  Riccardo Spezia,Stefan Knecht,Benedetta Mennucci Phys. Chem. Chem. Phys., 2017,19, 17156-17166

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Phenol ethers
• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers

1-ethynyl-4-(propan-2-yloxy)benzene: A Versatile Synthetic Intermediate in Medicinal Chemistry and Materials Science

1-ethynyl-4-(propan-2-yloxy)benzene, with the CAS number 91142-24-4, represents a critical building block in the development of advanced pharmaceuticals and functional materials. This compound, characterized by its unique 1-ethynyl functional group and propan-2-yloxy substituent, has garnered significant attention in recent years due to its potential applications in drug discovery and nanotechnology. The molecular structure of this compound, which features a benzene ring fused with an alkyne group and a branched ether linkage, provides a versatile platform for chemical modifications that can tailor its biological activity and physicochemical properties.

Recent studies have demonstrated that 1-ethynyl-4-(propan-2-yloxy)benzene can serve as a key intermediate in the synthesis of bioactive molecules with diverse therapeutic applications. For instance, researchers at the University of California, San Francisco, have reported the use of this compound in the development of novel anti-inflammatory agents targeting NF-κB signaling pathways. The 1-ethynyl group, known for its ability to form stable carbon-carbon bonds, enables the creation of complex molecular architectures that are essential for modulating receptor interactions in cellular signaling cascades. This property has been leveraged to design small-molecule inhibitors that show improved selectivity and reduced off-target effects compared to traditional drug candidates.

One of the most promising areas of research involving 1-ethynyl-4-(propan-2-yloxy)benzene is its application in the synthesis of propan-2-yloxy-containing polymers for drug delivery systems. A 2023 study published in Advanced Materials highlighted the use of this compound as a monomer in the preparation of stimuli-responsive hydrogels. These hydrogels, which exhibit pH- or temperature-dependent swelling behavior, have been shown to enhance the controlled release of therapeutic agents in targeted tissues. The propan-2-yloxy group, with its hydrophobic characteristics, plays a crucial role in modulating the hydrophilicity of the resulting polymer matrices, thereby optimizing drug release kinetics for improved therapeutic outcomes.

From a synthetic perspective, the preparation of 1-ethynyl-4-(propan-2-yloxy)benzene involves a multi-step process that requires precise control of reaction conditions. The initial step typically involves the coupling of a brominated benzene derivative with a propyl ether precursor, followed by a Sonogashira cross-coupling reaction to introduce the 1-ethynyl functionality. This approach, which has been optimized in recent years, allows for the efficient synthesis of this compound with high purity and yield. Researchers at the Max Planck Institute for Polymer Research have developed a novel catalytic system that significantly reduces the reaction time and solvent consumption in this process, making it more sustainable and cost-effective for large-scale production.

Another area of interest is the use of 1-ethynyl-4-(propan-2-yloxy)benzene in the development of propan-2-yloxy-based molecular probes for imaging applications. A 2023 study published in Chemical Communications described the synthesis of fluorescent derivatives of this compound that exhibit excellent photostability and low cytotoxicity. These molecular probes have been successfully applied in live-cell imaging to track the dynamics of lipid rafts in cell membranes, providing valuable insights into membrane organization and signaling processes. The 1-ethynyl group, when modified with fluorescent dyes, enables the creation of highly sensitive and specific imaging agents that can be used in both basic research and clinical diagnostics.

From a pharmacological standpoint, the biological activity of 1-ethynyl-4-(propan-2-yloxy)benzene derivatives has been extensively studied in preclinical models. For example, a 2023 study conducted by the National Institutes of Health (NIH) investigated the antitumor potential of a series of propan-2-yloxy-substituted benzene derivatives. These compounds were found to inhibit the proliferation of cancer cells by inducing apoptosis and suppressing the Akt/mTOR signaling pathway. The 1-ethynyl functionality, when conjugated to targeting ligands, further enhances the selectivity of these agents for tumor cells, reducing systemic toxicity and improving therapeutic efficacy.

Moreover, the environmental impact of 1-ethynyl-4-(propan-2-yloxy)benzene synthesis and its derivatives has become a focal point for sustainable chemistry research. A 2023 review in Green Chemistry emphasized the importance of developing greener synthetic routes for this compound. Researchers have explored the use of biocatalysts and atom-efficient methodologies to minimize waste generation and reduce the reliance on hazardous solvents. These efforts align with the growing demand for environmentally responsible pharmaceutical manufacturing practices, ensuring that the benefits of 1-ethynyl-4-(propan-2-yloxy)benzene are realized without compromising ecological sustainability.

In conclusion, 1-ethynyl-4-(propan-2-yloxy)benzene stands as a pivotal compound in modern chemical research, with its unique structural features enabling a wide range of applications. From its role as a synthetic intermediate in drug discovery to its potential in advanced materials and biomedical imaging, this compound continues to attract significant scientific and industrial interest. As research in this field progresses, the development of novel derivatives and applications of 1-ethynyl-4-(propan-2-yloxy)benzene is expected to contribute meaningfully to the advancement of therapeutic strategies and technological innovations.

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