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3-Methoxybenzene-1,2-diamine

  • CAS No. 37466-89-0

  • Cat. No. CS-0149010
  • Purity≥95%
  • MDL No.MFCD08276903

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

3-Methoxybenzene-1,2-diamine|CS-0149010

Structure of 37466-89-0

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General Information

  • CAS No. 37466-89-0
  • Cat. No. CS-0149010
  • Purity ≥95%
  • MDL No. MFCD08276903
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀N₂O
  • Molecular Weight 138.17
  • Synonym(s) 2,3-Diaminoanisole
  • SMILES NC1=CC=CC(OC)=C1N

Description

3-Methoxybenzene-1,2-diamine delivers a bifunctional aromatic scaffold with enhanced solubility and stability under standard conditions. The para-methoxy group modulates electron density, while the adjacent amine functionalities enable direct coupling in cross-coupling or condensation reactions. This compound serves as a key intermediate in the synthesis of bioactive heterocycles and functionalized materials.

Application

3-Methoxybenzene-1,2-diamine serves as a versatile building block for heterocyclic synthesis, enabling efficient access to benzimidazoles and related scaffolds through condensation with carbonyl compounds. Its ortho-diamine functionality offers high reactivity in cyclization reactions, while the methoxy group provides moderate electron donation and enhances solubility. The compound exhibits good bench stability and is compatible with standard purification techniques, facilitating its use in medicinal chemistry campaigns and process development workflows.

Synthesis

  • Route1

    References

    • CURIS, INC. Patent: WO2006/50506 A1, 2006 ; Location in patent: Page/Page column 126 ;
  • Route2

    References

    • Zhou, Jie; Jin, Jing; Zhang, Yi; Yin, Yuwen; Chen, Xiaoguang; Xu, Bailing European Journal of Medicinal Chemistry, 2013 , vol. 68, p. 222 - 232
  • Route3
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      16315-07-4
    • ~%
    • In-stock
      3-Methoxybenzene-1,2-diamine|CS-0149010
      37466-89-0

    References

    • Ricci,A.; Vivarelli,P. Gazzetta Chimica Italiana, 1967 , vol. 97, p. 750 - 757

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-H312-H315-H319-H332-H335
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P341-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P363-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   61.27
  • LogP   0.8596
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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