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CS-W001157 4
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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

  • CAS No. 380151-86-0

  • Cat. No. CS-W000922
  • Purity≥97%
  • MDL No.MFCD05663872

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

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde|CS-W000922

Structure of 380151-86-0

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General Information

  • CAS No. 380151-86-0
  • Cat. No. CS-W000922
  • Purity ≥97%
  • MDL No. MFCD05663872
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇BO₃
  • Molecular Weight 232.08
  • Synonym(s) Benzaldehyde, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
  • SMILES O=Cc1cccc(c1)B1OC(C(O1)(C)C)(C)C

Description

This boronate-functionalized aldehyde integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, offering high stability and compatibility with diverse reaction conditions. The tetramethylcyclohexadienone moiety enhances reactivity while maintaining bench-stable handling properties.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. The aldehyde functionality enables direct functionalization or derivatization, while the sterically protected dioxaborolane group ensures excellent stability, ease of handling, and compatibility with diverse reaction conditions. This reagent facilitates efficient construction of biaryl and aryl-aldehyde scaffolds commonly found in pharmaceutical intermediates and functional materials.

Synthesis

  • Route1

    References

    • CHROMA THERAPEUTICS LTD; DAVIES, Stephen John; PINTAT, Stéphane; NORTH, Carl Leslie; MOFFAT, David Festus Charles Patent: WO2014/1802 A1, 2014 ; Location in patent: Page/Page column 39; 40 ;
  • Route2

    References

    • Chow, Wing Kin; Yuen, On Ying; So, Chau Ming; Wong, Wing Tak; Kwong, Fuk Yee Journal of Organic Chemistry, 2012 , vol. 77, # 7 p. 3543 - 3548
  • Route3
    • null|null
      1448723-42-9
    • ~81%
    • In-stock
      3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde|CS-W000922
      380151-86-0

    References

    • Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   35.53
  • LogP   1.7983
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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