Cas no 140614-17-1 ((3,3-dimethylbutyl)boronic acid)

(3,3-Dimethylbutyl)boronic acid is an organoboron compound characterized by its branched alkyl chain and boronic acid functional group. This reagent is primarily employed in Suzuki-Miyaura cross-coupling reactions, where its sterically hindered structure can enhance selectivity in forming carbon-carbon bonds. The tert-butyl substituent adjacent to the boronic acid group contributes to improved stability, reducing protodeboronation side reactions. It is particularly useful in pharmaceutical and agrochemical synthesis, where controlled coupling of sterically demanding substrates is required. The compound is typically handled under inert conditions due to its sensitivity to moisture and oxygen. Its consistent reactivity and structural features make it a valuable intermediate in complex organic transformations.
(3,3-dimethylbutyl)boronic acid structure
140614-17-1 structure
Product Name:(3,3-dimethylbutyl)boronic acid
CAS No:140614-17-1
MF:C6H15BO2
MW:129.993102312088
MDL:MFCD06212378
CID:1298939
PubChem ID:10920536
Update Time:2025-05-24

(3,3-dimethylbutyl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • Boronic acid, (3,3-dimethylbutyl)-
    • 3,3-dimethylbutylboronic acid
    • tBuCH2CH2B(OH)2
    • (3,3-dimethylbutyl)boronic acid
    • EN300-3178811
    • AKOS013015349
    • 140614-17-1
    • MDL: MFCD06212378
    • Inchi: 1S/C6H15BO2/c1-6(2,3)4-5-7(8)9/h8-9H,4-5H2,1-3H3
    • InChI Key: BZZGWDSWJYJBJL-UHFFFAOYSA-N
    • SMILES: OB(CCC(C)(C)C)O

Computed Properties

  • Exact Mass: 129.12015
  • Monoisotopic Mass: 130.1165099g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 3
  • Complexity: 75.6
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 40.5?2

Experimental Properties

  • PSA: 40.46

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Additional information on (3,3-dimethylbutyl)boronic acid

Introduction to (3,3-dimethylbutyl)boronic Acid (CAS No. 140614-17-1)

(3,3-dimethylbutyl)boronic acid, with the chemical formula C7H14O2 and CAS number 140614-17-1, is a significant compound in the field of organoboron chemistry. This boronic acid derivative has garnered considerable attention due to its unique structural properties and versatile applications in synthetic chemistry, pharmaceuticals, and materials science. The presence of two methyl groups at the terminal carbon of the butyl chain enhances its steric bulk, making it a valuable reagent in cross-coupling reactions and as a protecting group for boronic acids.

Boronic acids are well-known for their role in Suzuki-Miyaura cross-coupling reactions, which are pivotal in constructing carbon-carbon bonds in organic synthesis. The steric hindrance provided by the (3,3-dimethylbutyl) group in (3,3-dimethylbutyl)boronic acid allows for selective reactions with less hindered boronic acids or halides, improving yields and reducing side reactions. This characteristic has made it a preferred choice in pharmaceutical synthesis, where high selectivity and efficiency are crucial.

In recent years, (3,3-dimethylbutyl)boronic acid has been explored in the development of novel drug candidates. Its ability to participate in cross-coupling reactions enables the formation of complex molecular architectures that are often found in bioactive compounds. For instance, researchers have utilized this compound to synthesize boron-containing heterocycles, which have shown promise as kinase inhibitors and antiviral agents. The steric environment provided by the bulky substituents can influence the binding affinity of these compounds to their biological targets, making (3,3-dimethylbutyl)boronic acid a valuable tool in medicinal chemistry.

Beyond pharmaceutical applications, (3,3-dimethylbutyl)boronic acid has found utility in materials science. Its incorporation into polymers and coatings can enhance thermal stability and mechanical properties. Additionally, its reactivity with transition metals makes it a candidate for catalytic processes in polymerization reactions. The growing interest in sustainable chemistry has also led to investigations into green synthesis methods for this compound, focusing on reducing waste and improving atom economy.

The latest research highlights several innovative uses of (3,3-dimethylbutyl)boronic acid. For example, studies have demonstrated its effectiveness in the synthesis of conjugated polymers for organic electronics. These polymers exhibit excellent charge transport properties, which are essential for applications such as organic light-emitting diodes (OLEDs) and photovoltaic cells. The bulky nature of the substituents helps to prevent aggregation of polymer chains, leading to better film formation and device performance.

Another emerging application is in the field of click chemistry, where (3,3-dimethylbutyl)boronic acid serves as a versatile building block for constructing complex molecules under mild conditions. Its compatibility with other click chemistry components allows for rapid assembly of functional materials without compromising purity or yield. This has opened new avenues for drug discovery and material design.

In conclusion, (3,3-dimethylbutyl)boronic acid is a multifaceted compound with significant implications across multiple scientific disciplines. Its unique structural features make it an indispensable reagent in synthetic organic chemistry, particularly in cross-coupling reactions that form the backbone of modern drug development. Furthermore, its applications in materials science continue to expand, driven by the demand for advanced functional materials with enhanced properties. As research progresses, we can expect even more innovative uses for this remarkable boronic acid derivative.

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