• 1. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
• 2. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 3. Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples?
  Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248
• 4. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 5. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Oxazoles 2,5-disubstituted oxazoles

Introduction to 2-cyclopropyloxazole-5-carbaldehyde (CAS No. 1267443-15-1)

2-cyclopropyloxazole-5-carbaldehyde, identified by the Chemical Abstracts Service Number (CAS No.) 1267443-15-1, is a significant compound in the realm of organic chemistry and pharmaceutical research. This heterocyclic aldehyde features a cyclopropyl group attached to an oxazole ring, which is further functionalized with a formyl group at the 5-position. The unique structural attributes of this molecule make it a valuable intermediate in synthetic chemistry and a potential building block for various pharmacologically active agents.

The cyclopropyloxazole core is particularly noteworthy due to its rigid bicyclic structure, which can influence both the electronic properties and steric environment of the molecule. The presence of the aldehyde functionality (–CHO) at the 5-position of the oxazole ring introduces reactivity that is amenable to further chemical transformations, such as condensation reactions, reduction, or oxidation processes. These characteristics have positioned 2-cyclopropyloxazole-5-carbaldehyde as a subject of interest in medicinal chemistry and materials science.

In recent years, there has been growing interest in oxazole derivatives due to their diverse biological activities. Oxazoles are known for their role as scaffolds in drug discovery, exhibiting properties such as antimicrobial, anti-inflammatory, and anticonvulsant effects. The incorporation of a cyclopropyl group into the oxazole framework can modulate these activities by altering electronic distributions and steric interactions. Specifically, the 2-cyclopropyloxazole-5-carbaldehyde structure may serve as a precursor for synthesizing novel compounds with enhanced pharmacological profiles.

One of the most compelling aspects of 2-cyclopropyloxazole-5-carbaldehyde is its utility in constructing more complex molecules through cross-coupling reactions, such as Suzuki-Miyaura or Heck couplings. The aldehyde group can readily participate in these transformations, allowing chemists to attach aryl or vinyl groups and generate derivatives with tailored properties. Such modifications are crucial in developing new therapeutic agents where specific biological targets require precise molecular architectures.

Recent advancements in synthetic methodologies have enabled more efficient access to 2-cyclopropyloxazole-5-carbaldehyde and its derivatives. For instance, transition-metal-catalyzed reactions have been employed to streamline the construction of the cyclopropyloxazole core, reducing reaction times and improving yields. These innovations are particularly relevant in industrial settings where scalability and cost-effectiveness are paramount.

The pharmaceutical industry has shown particular interest in heterocyclic compounds due to their prevalence in natural products and known drug entities. 2-cyclopropyloxazole-5-carbaldehyde fits into this category as it combines elements that are often associated with bioactivity—oxazoles, cyclopropanes, and aldehydes. Researchers are exploring its potential as a precursor for kinase inhibitors, which play a critical role in treating cancers and inflammatory diseases. The cyclopropyl moiety, in particular, has been linked to improved binding affinity and selectivity in drug-like molecules.

In addition to its pharmaceutical applications, 2-cyclopropyloxazole-5-carbaldehyde has found utility in materials science. The unique electronic properties of this compound make it a candidate for organic semiconductors or luminescent materials. Its ability to undergo further functionalization allows for the design of materials with specific optoelectronic characteristics, which could be beneficial in display technologies or sensors.

The synthesis of 2-cyclopropyloxazole-5-carbaldehyde typically involves multi-step processes that begin with readily available precursors such as 2-hydroxyoxazole or cyclopropanecarboxaldehyde. Advanced techniques like organometallic chemistry have been employed to achieve regioselective transformations, ensuring that the formyl group is introduced at the desired position on the oxazole ring. These synthetic strategies highlight the compound's importance as a synthetic intermediate.

Evaluation of 2-cyclopropyloxazole-5-carbaldehyde often involves spectroscopic methods such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and infrared (IR) spectroscopy to confirm its structure and purity. Additionally, computational studies have been utilized to predict its reactivity and potential interactions with biological targets. These approaches provide valuable insights into how modifications to the molecule might influence its behavior in vitro or in vivo.

The future prospects for 2-cyclopropyloxazole-5-carbaldehyde are promising, given its versatility as a building block. As research continues to uncover new applications for oxazole derivatives, compounds like this one are likely to play an increasingly important role in drug discovery and material development. Collaborative efforts between academia and industry will be essential to fully realize their potential.

• 153138-05-7(5-Oxazolecarboxaldehyde,2-methyl-, ion(1-))
• 885273-42-7(2-methyl-1,3-oxazole-5-carbaldehyde)
• 1263378-39-7(2-cyclopropyl-1,3-oxazole-5-carboxylic acid)
• 1211592-95-8(2-cyclopropyloxazole-5-carbonitrile)
• 288092-92-2(OXAZOLE, 5-METHYL-2-PENTYL-)
• 808737-45-3(Oxazole,5-methyl-2-tricyclo[3.3.1.13,7]dec-1-yl-)
• 110788-50-6(Oxazole, 5-methyl-2-(1-methylethyl)-)
• 16400-62-7(Oxazole, 2-hexyl-5-methyl-)
• 1216002-44-6(2-tert-butyl-1,3-oxazole-5-carboxylic acid)
• 1126634-01-2(2-ethyl-1,3-oxazole-5-carbaldehyde)