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N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

  • CAS No. 920304-57-0

  • Cat. No. CS-0176004
  • Purity≥98%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0176004

Structure of 920304-57-0

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General Information

  • CAS No. 920304-57-0
  • Cat. No. CS-0176004
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₆BNO₂
  • Molecular Weight 275.19
  • Synonym(s) 4-(Diethylamino)phenylboronic Acid Pinacol Ester
  • SMILES CCN(C1=CC=C(B2OC(C)(C(C)(O2)C)C)C=C1)CC

Description

N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling under mild conditions. The diethylamino moiety imparts enhanced solubility and electron-donating character, while the tetramethylcyclopentadienone scaffold ensures high stability and moisture tolerance. This reagent integrates seamlessly into complex molecule synthesis workflows.

Application

N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boron-containing building block in Suzuki-Miyaura cross-coupling reactions. The diborane moiety enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the N,N-diethyl amine group enhances solubility and stability. This compound facilitates the construction of biaryl scaffolds with high functional group tolerance and is well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      74-96-4
    • In-stock
      4-Aminophenylboronic acid pinacol ester|CS-M0336
      214360-73-3
    • ~%
    • In-stock
      N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0176004
      920304-57-0

    References

    • HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; JI, Jianguo Patent: WO2012/167423 A1, 2012 ; Location in patent: Page/Page column 35 ; WO 2012/167423 A1
  • Route2
    • null|null
      75-03-6
    • In-stock
      4-Aminophenylboronic acid pinacol ester|CS-M0336
      214360-73-3
    • ~%
    • In-stock
      N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0176004
      920304-57-0

    References

    • Irm LLC Patent: US2009/75996 A1, 2009 ; Location in patent: Page/Page column 33 ;
  • Route3
    • null|null
      61676-62-8
    • In-stock
      4-Bromo-N,N-diethylaniline|CS-0168158
      2052-06-4
    • ~50%
    • In-stock
      N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0176004
      920304-57-0

    References

    • Park, Byung Sun; El-deeb, Ibrahim M.; Yoo, Kyung Ho; Han, Dong Keun; Tae, Jin Sung; Lee, So Ha Bulletin of the Korean Chemical Society, 2012 , vol. 33, # 11 p. 3629 - 3634

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   21.7
  • LogP   2.832
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   4

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