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CS-W001157 4
Total: USD 88.00

Benzoic acid, 4-borono-3-methyl-, 1-methyl ester

  • CAS No. 158429-38-0

  • Cat. No. CS-0030805
  • Purity≥98%
  • MDL No.MFCD16036117

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

Benzoic acid, 4-borono-3-methyl-, 1-methyl ester|CS-0030805

Structure of 158429-38-0

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General Information

  • CAS No. 158429-38-0
  • Cat. No. CS-0030805
  • Purity ≥98%
  • MDL No. MFCD16036117
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁BO₄
  • Molecular Weight 193.99
  • Synonym(s) (4-(Methoxycarbonyl)-2-methylphenyl)boronic acid
  • SMILES COC(C1=CC(C)=C(B(O)O)C=C1)=O

Description

This boronic acid features a methoxycarbonyl group at the 4-position and a methyl substituent at the 2-position, enabling selective coupling in Suzuki-Miyaura reactions. The electron-deficient aryl ring enhances reactivity while maintaining bench-stable handling under standard conditions.

Application

4-(Methoxycarbonyl)-2-methylphenylboronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. Its ortho-methyl and ester functionalities provide enhanced stability and facilitate downstream derivatization, while the boronic acid group offers excellent functional group tolerance and reliable coupling efficiency under standard reaction conditions.

Synthesis

  • Route1

    References

    • MERCK and CO., INC. Patent: WO2008/82567 A1, 2008 ; Location in patent: Page/Page column 6 ;
  • Route2

    References

    • Imanishi, Masashi; Tomishima, Yasuyo; Itou, Shinji; Hamashima, Hitoshi; Nakajima, Yutaka; Washizuka, Kenichi; Sakurai, Minoru; Matsui, Shigeo; Imamura, Emiko; Ueshima, Koji; Yamamoto, Takao; Yamamoto, Nobuhiro; Ishikawa, Hirofumi; Nakano, Keiko; Unami, Naoko; Hamada, Kaori; Matsumura, Yasuhiro; Takamura, Fujiko; Hattori, Kouji Journal of Medicinal Chemistry, 2008 , vol. 51, # 6 p. 1925 - 1944
  • Route3

    References

    • Stones, Duane; Manku, Sukhdev; Lu, Xiaosong; Hall, Dennis G. Chemistry - A European Journal, 2004 , vol. 10, # 1 p. 92 - 100

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   66.76
  • LogP   -0.53858
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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