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3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

  • CAS No. 269409-74-7

  • Cat. No. CS-B1244
  • Purity≥98%
  • MDL No.MFCD08061640

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

3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid|CS-B1244

Structure of 269409-74-7

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General Information

  • CAS No. 269409-74-7
  • Cat. No. CS-B1244
  • Purity ≥98%
  • MDL No. MFCD08061640
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₉BO₄
  • Molecular Weight 262.11
  • Synonym(s) None
  • SMILES O=C(O)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C(C)=C1

Description

3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid features a boronate ester group enabling reliable Suzuki-Miyaura coupling under mild conditions. The carboxylic acid functionality offers direct handle for derivatization, while the tetramethyl-substituted dioxaborolane enhances stability and shelf life. This ortho-functionalized scaffold integrates seamlessly into complex molecular architectures.

Application

3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. The pinacol boronate ester group enables efficient C–C bond formation under mild conditions, while the carboxylic acid functionality provides a handle for derivatization or conjugation. Bench-stable and compatible with a wide range of functional groups, it facilitates rapid access to substituted biaryls and complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • LABORATORIOS ALMIRALL, S.A. Patent: WO2007/96072 A2, 2007 ; Location in patent: Page/Page column 36 ; WO 2007/096072 A2
  • Route2

    References

    • GLAXO GROUP LIMITED Patent: WO2007/147109 A2, 2007 ; Location in patent: Page/Page column 180-181 ; WO 2007/147109 A2
  • Route3
    • In-stock
      4-Iodo-3-methylbenzoic acid|CS-0099438
      52107-87-6
    • null|null
      25015-63-8
    • ~86%
    • In-stock
      3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid|CS-B1244
      269409-74-7

    References

    • Commonwealth Scientific and Industrial Research Organisation Patent: US6680401 B1, 2004 ; Location in patent: Page column 21-22 ;

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   55.76
  • LogP   1.99242
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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