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CS-W001157 4
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Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate

  • CAS No. 944392-68-1

  • Cat. No. CS-W001005
  • Purity≥98%
  • MDL No.MFCD11858596

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

Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate|CS-W001005

Structure of 944392-68-1

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General Information

  • CAS No. 944392-68-1
  • Cat. No. CS-W001005
  • Purity ≥98%
  • MDL No. MFCD11858596
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₁BO₆
  • Molecular Weight 320.15
  • Synonym(s) Dimethyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzenedicarboxylate
  • SMILES O=C(OC)C1=CC(=CC(=C1)C(=O)OC)B2OC(C)(C)C(O2)(C)C

Description

Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate features a boronate ester group flanked by two methyl ester functionalities, enabling efficient Suzuki-Miyaura cross-coupling under mild conditions. This bench-stable reagent integrates readily into complex molecular architectures, offering high functional group tolerance and predictable reactivity.

Application

Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate serves as a versatile boronate building block for Suzuki-Miyaura coupling reactions. The sterically protected bis(pinacolato)boron group enables high stability, mild reaction conditions, and excellent functional group tolerance. It facilitates efficient construction of biaryl and heteroaryl scaffolds in medicinal chemistry and materials science workflows, with straightforward purification and compatibility across gram-scale syntheses.

Synthesis

  • Route1

    References

    • Park, Jinhee; Wang, Zhiyong U.; Sun, Lin-Bing; Chen, Ying-Pin; Zhou, Hong-Cai Journal of the American Chemical Society, 2012 , vol. 134, # 49 p. 20110 - 20116
  • Route2

    References

    • Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; Patel, Nitinchandra D.; Yee, Nathan K.; Senanayake, Chris H. Organic Letters, 2011 , vol. 13, # 6 p. 1366 - 1369
  • Route3
    • In-stock
      Dimethyl 5-iodoisophthalate|CS-W005045
      51839-15-7
    • null|null
      25015-63-8
    • ~49%
    • In-stock
      Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate|CS-W001005
      944392-68-1

    References

    • Muthiah, Chinnasamy; Taniguchi, Masahiko; Kim, Han-Je; Schmidt, Izabela; Kee, Hooi Ling; Holten, Dewey; Bocian, David F.; Lindsey, Jonathan S. Photochemistry and Photobiology, 2007 , vol. 83, # 6 p. 1513 - 1528

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

Quality Control

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Computational Chemistry Data

  • TPSA   71.06
  • LogP   1.559
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   3

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