Cas no 1068163-32-5 (4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane)

4,4,5,5-Tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane is a specialized boronic ester derivative featuring a tetra-substituted dioxaborolane core and a propargyl ether linkage. Its key advantages include enhanced stability due to the tetramethyl substitution on the borolane ring, which mitigates hydrolysis and oxidative degradation. The oxan-2-yloxypropynyl moiety provides a reactive alkyne handle for further functionalization, making it valuable in cross-coupling reactions, particularly Sonogashira and Suzuki-Miyaura couplings. The protected hydroxyl group in the tetrahydropyranyl (THP) ether enhances solubility in organic solvents while allowing deprotection under mild acidic conditions. This compound is particularly useful in synthetic organic chemistry for constructing complex molecular architectures with precise boron incorporation.
4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane structure
1068163-32-5 structure
Product Name:4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane
CAS No:1068163-32-5
MF:C14H23BO4
MW:266.141024827957
MDL:MFCD31742969
CID:4488708
PubChem ID:135039233
Update Time:2025-05-23

4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane Chemical and Physical Properties

Names and Identifiers

    • 2H-Pyran, tetrahydro-2-[[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propyn-1-yl]oxy]-
    • 4,4,5,5-tetramethyl-2-(3-((tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-yl)-1,3,2-dioxaborolane
    • 4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane
    • 4,4,5,5-tetramethyl-2-(3-(oxan-2-yloxy)prop-1-yn-1-yl)-1,3,2-dioxaborolane
    • EN300-22906518
    • Z3153429952
    • 872-842-4
    • 1068163-32-5
    • 4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-ynyl]-1,3,2-dioxaborolane
    • MDL: MFCD31742969
    • Inchi: 1S/C14H23BO4/c1-13(2)14(3,4)19-15(18-13)9-7-11-17-12-8-5-6-10-16-12/h12H,5-6,8,10-11H2,1-4H3
    • InChI Key: AKGDTLXVMYMZQJ-UHFFFAOYSA-N
    • SMILES: O1C(C)(C)C(C)(C)OB1C#CCOC1OCCCC1

Computed Properties

  • Exact Mass: 266.1689394Da
  • Monoisotopic Mass: 266.1689394Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 3
  • Complexity: 363
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 36.9?2

4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
NAN JING YAO SHI KE JI GU FEN Co., Ltd.
PBJL100248-100MG
4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane
1068163-32-5 95%
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¥ 963.00 2023-04-03
NAN JING YAO SHI KE JI GU FEN Co., Ltd.
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¥ 1,537.00 2023-04-03
NAN JING YAO SHI KE JI GU FEN Co., Ltd.
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Additional information on 4,4,5,5-tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane

4,4,5,5-Tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane: A Comprehensive Overview

4,4,5,5-Tetramethyl-2-[3-(oxan-2-yloxy)prop-1-yn-1-yl]-1,3,2-dioxaborolane, also known by its CAS number 1068163-32-5, is a highly specialized organic compound with significant applications in various fields of chemistry. This compound belongs to the class of dioxaborolanes, which are known for their unique chemical properties and versatility in synthetic chemistry. The structure of this compound is characterized by a dioxaborolane ring system with specific substituents that confer it with distinct reactivity and functionality.

The molecular structure of 4,4,5,5-tetramethyl groupings suggests a high degree of steric hindrance around the boron atom. This steric environment plays a crucial role in determining the compound's chemical behavior. The presence of the oxan-2-yloxy group attached to a propargyl chain introduces additional complexity to the molecule. Recent studies have highlighted the importance of such functional groups in mediating specific chemical transformations, particularly in organoboron chemistry.

One of the most notable applications of this compound is in the field of catalytic processes. Researchers have demonstrated that this dioxaborolane derivative can act as an efficient catalyst in certain types of cross-coupling reactions. For instance, its ability to facilitate Suzuki-Miyaura couplings under mild conditions has been extensively reported in recent literature. This makes it a valuable tool in the synthesis of complex organic molecules with high precision and yield.

In addition to its catalytic applications, this compound has also found utility in materials science. Its unique electronic properties make it a promising candidate for use in advanced materials such as semiconductors and optoelectronic devices. Recent advancements in nanotechnology have further expanded its potential applications, particularly in the development of nanostructured materials with tailored properties.

The synthesis of 4,4,5,5-tetramethyl-substituted dioxaborolanes has been a topic of considerable interest among chemists. Various synthetic routes have been explored to optimize the production process. One such method involves the use of transition metal catalysts to facilitate the formation of the dioxaborolane ring system under controlled conditions. These methods not only enhance the efficiency of synthesis but also contribute to the overall sustainability of chemical processes.

From an environmental standpoint, understanding the degradation pathways and ecological impact of this compound is essential. Recent studies have focused on evaluating its biodegradability and toxicity profiles under various environmental conditions. These findings are critical for ensuring safe handling and disposal practices within industrial settings.

In conclusion, 4,4,5,5-tetramethyl-dioxaborolane derivatives represent a fascinating class of compounds with diverse applications across multiple disciplines. Ongoing research continues to uncover new insights into their chemical behavior and potential uses. As our understanding of these compounds deepens, they are poised to play an even more significant role in advancing modern chemistry and materials science.

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