• 1. An artificial blood vessel implanted three-dimensional microsystem for modeling transvascular migration of tumor cells?
  Xue-Ying Wang,Ying Pei,Min Xie,Zi-He Jin,Ya-Shi Xiao,Yang Wang,Li-Na Zhang,Yan Li,Wei-Hua Huang Lab Chip, 2015,15, 1178-1187
• 2. An insight into the origin of room-temperature ferromagnetism in SnO2 and Mn-doped SnO2 quantum dots: an experimental and DFT approach?
  Dhamodaran Manikandan,S. Amirthapandian,I. S. Zhidkov,A. I. Kukharenko,S. O. Cholakh,Ramaswamy Murugan Phys. Chem. Chem. Phys., 2018,20, 6500-6514
• 3. An atom-economical protocol for direct conversion of Baylis–Hillman alcohols to β-chloro aldehydes in water?
  Raktani Bikshapathi,Sai Prathima Parvathaneni,Vaidya Jayathirtha Rao Green Chem., 2017,19, 4446-4450
• 4. An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells?
  Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang Cheng Food Funct., 2020,11, 10635-10644
• 5. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877

Introduction to 4,4,5,5-tetramethyl-2-pent-1-ynyl-1,3,2-dioxaborolane (CAS No. 634196-62-6)

4,4,5,5-tetramethyl-2-pent-1-ynyl-1,3,2-dioxaborolane, identified by its Chemical Abstracts Service (CAS) number 634196-62-6, is a specialized organoboron compound that has garnered significant attention in the field of synthetic chemistry and pharmaceutical research. This compound belongs to the class of boron-containing heterocycles, which are widely recognized for their utility in cross-coupling reactions and as intermediates in the synthesis of complex molecular architectures. The unique structural features of this compound, including its tetramethyl substituents and the presence of a pent-1-yne moiety, contribute to its distinctive reactivity and make it a valuable tool in modern chemical synthesis.

The dioxaborolane core of this molecule is particularly noteworthy, as it serves as an effective boronic ester equivalent that participates in various transition-metal-catalyzed reactions. These reactions are foundational in the construction of carbon-carbon bonds, a critical step in the development of novel pharmaceuticals and agrochemicals. The stability and functional versatility of 4,4,5,5-tetramethyl-2-pent-1-ynyl-1,3,2-dioxaborolane make it an attractive candidate for applications in both academic research and industrial-scale synthesis.

In recent years, there has been a surge in the exploration of boron-containing compounds due to their enhanced bioactivity and metabolic stability. The pent-1-yne substituent in this molecule introduces a linear alkyne functionality, which can be further modified through various chemical transformations. This flexibility allows chemists to tailor the compound for specific applications, such as the synthesis of biologically active molecules or advanced materials. The tetramethyl groups provide steric hindrance and electronic modulation, influencing the overall reactivity and selectivity of the molecule.

One of the most compelling aspects of 4,4,5,5-tetramethyl-2-pent-1-ynyl-1,3,2-dioxaborolane is its role in facilitating cross-coupling reactions. These reactions are pivotal in organic synthesis because they enable the efficient assembly of complex structures from simpler precursors. The Suzuki-Miyaura coupling, for instance, is a widely used reaction that leverages boronic acids or esters to form carbon-carbon bonds under mild conditions. The boronic ester functionality derived from the dioxaborolane core allows this compound to participate seamlessly in such reactions.

The pharmaceutical industry has been particularly keen on exploring new boron-containing entities due to their potential therapeutic benefits. Boronated compounds have shown promise in various therapeutic areas, including oncology and anti-inflammatory treatments. The structural motif of 4,4,5,5-tetramethyl-2-pent-1-ynyl-1,3,2-dioxaborolane aligns well with these interests because it combines stability with reactivity—key attributes for drug candidates. Researchers have been investigating how modifications to this scaffold can enhance its pharmacological properties while maintaining synthetic feasibility.

Recent advancements in computational chemistry have also contributed to a deeper understanding of how 4,4,5,5-tetramethyl-2-pent-1-ynyl-1,3,2-dioxaborolane behaves in different reaction environments. Molecular modeling studies have revealed insights into its electronic structure and how it interacts with transition metals during catalytic processes. These insights are invaluable for optimizing reaction conditions and improving yields—a critical consideration for large-scale production.

The synthesis of 4,4,5,5-tetramethyl-2-pent-1-ynyl-1,3,2-dioxaborolane itself presents an interesting challenge due to its complex architecture. However, chemists have developed robust synthetic routes that highlight its accessibility without compromising purity or yield. These methods often involve multi-step sequences that showcase the compound's versatility as a building block. For instance, palladium-catalyzed Sonogashira couplings can be employed to introduce the alkyne functionality, followed by functionalization at other positions on the molecule.

The applications of this compound extend beyond pharmaceuticals into materials science. Boron-containing polymers, for example, exhibit unique properties such as high thermal stability and electrical conductivity, making them suitable for advanced electronic devices. The ability to incorporate 4, 4, 5, 5-tetramethyl- 2-pent- 1- ynyl- 1, 3, 2- dioxaborolane into these materials could lead to novel functional polymers with enhanced performance characteristics.

As research continues, new derivatives of 4, 4, 5, 5-tetramethyl- 2-pent- 1- ynyl- 1, 3, 2- dioxaborolane are likely to emerge. These derivatives may exhibit improved reactivity or selectivity, opening up new avenues for synthetic applications. Additionally, green chemistry principles are being increasingly integrated into boron chemistry research, with efforts focused on developing more sustainable synthetic methods that minimize waste and hazardous byproducts.

In conclusion,4， 4， 5， 5-tetramethyl- 2-pent- 1- ynyl- 1， 3， 2- dioxaborolane (CAS No. 634196-62-6) is a versatile and highly functional organoboron compound with broad applications across multiple scientific disciplines. Its unique structural features make it an indispensable tool for synthetic chemists seeking to construct complex molecular architectures. As research progresses， this compound is expected to play an even greater role in advancing both academic knowledge and industrial innovation.

• 159087-47-5(1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(3-methyl-1-pentynyl)-)
• 121021-21-4(Boronic acid, 1-hexynyl-, bis(1-methylethyl) ester)
• 159087-42-0(5-Chloropent-1-ynylboronic acid, pinacol ester)
• 347389-74-6(2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 159087-41-9(2-(3,3-dimethyl-1-butyn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 159087-43-1(1,3,2-Dioxaborolane, 2-(cyclopentylethynyl)-4,4,5,5-tetramethyl-)
• 159087-40-8(2-(Hex-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 121021-25-8(Boronic acid, (cyclopentylethynyl)-, bis(1-methylethyl) ester)
• 121037-33-0(Boronic acid, 1-octynyl-, bis(1-methylethyl) ester)
• 634196-63-7(3-Methoxy-1-propyn-1-ylboronic Acid Pinacol Ester)