Cas no 325142-97-0 (N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide)

N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide is a boronic ester derivative commonly employed as an intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. The presence of the dioxaborolane group enhances stability and handling compared to free boronic acids, while maintaining reactivity under appropriate conditions. The diethylamide moiety contributes to improved solubility in organic solvents, facilitating its use in diverse reaction setups. This compound is valued for its compatibility with a range of functional groups and its role in constructing complex aryl-aryl bonds, making it useful in pharmaceutical and materials science research. Proper storage under inert conditions is recommended to preserve its integrity.
N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide structure
325142-97-0 structure
Product Name:N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
CAS No:325142-97-0
MF:C17H26BNO3
MW:303.204245090485
MDL:MFCD08458202
CID:829251
PubChem ID:329763738
Update Time:2025-06-12

N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Chemical and Physical Properties

Names and Identifiers

    • N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
    • [3-(Diethylamine-1-carbonyl)phenyl]-boronic acid pinacol ester
    • 3-(N,N-Diethylaminocarbonyl)phenylboronic acid, pinacol ester
    • N,N-DIETHYL-4-(-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZAMIDE
    • AMTB108
    • AT13107
    • DTXSID50592147
    • MFCD08458202
    • 3-(N,N-Diethylaminocarbonyl)phenylboronic acid pinacol ester
    • SCHEMBL15550347
    • AS-2342
    • J-018770
    • AKOS015960157
    • [3-(Diethylamine-1-carbonyl)phenyl]boronic acid pinacol ester
    • 3-(N,N-Diethylaminocarbonyl)phenylboronic acid pinacol ester, 95%
    • 4-(N,N-Diethylaminocarbonyl)phenylboronic acid,pinacol ester
    • 325142-97-0
    • CS-0130649
    • MDL: MFCD08458202
    • Inchi: 1S/C17H26BNO3/c1-7-19(8-2)15(20)13-10-9-11-14(12-13)18-21-16(3,4)17(5,6)22-18/h9-12H,7-8H2,1-6H3
    • InChI Key: XCMONACECYHFCP-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CC=C(C(N(CC)CC)=O)C=2)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 303.20100
  • Monoisotopic Mass: 303.2005739g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 5
  • Complexity: 391
  • 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: 38.8?2

Experimental Properties

  • Melting Point: 76-80?°C
  • PSA: 38.77000
  • LogP: 2.46780

N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: 26
  • Hazardous Material Identification: Xi
  • Storage Condition:Store at room temperature

N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Pricemore >>

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Additional information on N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Research Brief on N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (CAS: 325142-97-0)

N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (CAS: 325142-97-0) is a boronic ester derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry. This compound, often utilized as a key intermediate in Suzuki-Miyaura cross-coupling reactions, plays a pivotal role in the synthesis of complex organic molecules, particularly in the development of pharmaceuticals and bioactive compounds. Recent studies have highlighted its potential in drug discovery, especially in the design of kinase inhibitors and other targeted therapies.

The compound's unique structure, featuring a boronic ester moiety, enables its application in diverse chemical transformations. Researchers have explored its utility in the synthesis of arylboronic acids, which are crucial for the development of novel therapeutic agents. A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficacy of this compound in the synthesis of proteolysis-targeting chimeras (PROTACs), a groundbreaking approach in targeted protein degradation. The study underscored the compound's stability and reactivity, making it a valuable tool in medicinal chemistry.

In addition to its synthetic applications, N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide has been investigated for its potential biological activities. Preliminary in vitro studies have shown that derivatives of this compound exhibit moderate inhibitory effects on certain kinases involved in cancer progression. However, further research is required to elucidate its mechanism of action and optimize its pharmacological properties. The compound's low toxicity profile, as reported in a 2022 Toxicology Reports article, suggests its suitability for further preclinical development.

Recent advancements in analytical techniques have also facilitated the characterization of this compound. High-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy have been employed to confirm its purity and structural integrity. These techniques are essential for ensuring the reproducibility of synthetic protocols and the reliability of biological assays. A 2023 Analytical Chemistry publication highlighted the use of these methods in quality control processes for boronic ester derivatives, including CAS: 325142-97-0.

Despite its promising applications, challenges remain in the large-scale production and commercialization of N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide. Issues such as cost-effectiveness, scalability, and environmental impact need to be addressed to facilitate its widespread adoption in the pharmaceutical industry. Collaborative efforts between academia and industry are underway to develop greener synthetic routes and improve the compound's accessibility for research and development purposes.

In conclusion, N,N-Diethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (CAS: 325142-97-0) represents a versatile and valuable compound in chemical biology and medicinal chemistry. Its applications in drug discovery, particularly in the synthesis of kinase inhibitors and PROTACs, underscore its potential to contribute to the development of next-generation therapeutics. Ongoing research aims to further explore its biological activities and optimize its synthetic pathways, paving the way for its integration into clinical and industrial applications.

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