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CS-W001157 4
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3-Amino-2-methoxybenzoic acid

  • CAS No. 861306-04-9

  • Cat. No. CS-0099472
  • Purity≥98%
  • MDL No.MFCD09701221

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

3-Amino-2-methoxybenzoic acid|CS-0099472

Structure of 861306-04-9

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General Information

  • CAS No. 861306-04-9
  • Cat. No. CS-0099472
  • Purity ≥98%
  • MDL No. MFCD09701221
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉NO₃
  • Molecular Weight 167.16
  • Synonym(s) 3-Amino-o-anisic Acid
  • SMILES O=C(C1=CC=CC(N)=C1OC)O

Description

3-Amino-2-methoxybenzoic acid features a strategically positioned amino group and methoxy substituent on the benzene ring, enabling versatile conjugation and electronic tuning. This ortho-substituted scaffold delivers enhanced solubility and stability in polar solvents, facilitating efficient integration into pharmaceutical intermediates and bioactive molecule scaffolds under standard conditions.

Application

3-Amino-2-methoxybenzoic acid serves as a versatile building block for medicinal chemistry and heterocyclic synthesis, enabling direct functionalization at the amino and carboxylic acid sites. Its ortho-difunctionalized benzene core provides enhanced regiocontrol in coupling reactions and facilitates the construction of complex scaffolds. The methoxy group offers moderate stability and tunable reactivity, while the amine and acid functionalities allow for straightforward derivatization via amidation, esterification, or metal-catalyzed cross-coupling. Ideal for bench-scale applications requiring reliable handling and purification.

Synthesis

  • Route1
    • 5-Bromo-2-methoxy-3-nitrobenzoic acid|CS-0465959
      60541-89-1
    • ~96%
    • In-stock
      3-Amino-2-methoxybenzoic acid|CS-0099472
      861306-04-9

    References

    • Almstead, Neil G.; Hwang, Peter Seongwoo; Moon, Young-Choon; Welch, Ellen M. Patent: US2008/139632 A1, 2008 ; Location in patent: Page/Page column 19 ;
  • Route2

    References

    • Qin, Bo; Ong, Wei Qiang; Ye, Ruijuan; Du, Zhiyun; Chen, Xiuying; Yan, Yan; Zhang, Kun; Su, Haibin; Zeng, Huaqiang Chemical Communications, 2011 , vol. 47, # 19 p. 5419 - 5421
  • Route3
    • null|null
      912577-35-6
    • ~%
    • In-stock
      3-Amino-2-methoxybenzoic acid|CS-0099472
      861306-04-9

    References

    • Hu, Zilun; Jiang, Xiangjun; Han, Wei Tetrahedron Letters, 2008 , vol. 49, # 35 p. 5192 - 5195

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   72.55
  • LogP   0.9756
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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