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3-Chloro-5-methoxyphenol

  • CAS No. 65262-96-6

  • Cat. No. CS-D1537
  • Purity≥98%
  • MDL No.MFCD00002260

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

3-Chloro-5-methoxyphenol|CS-D1537

Structure of 65262-96-6

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General Information

  • CAS No. 65262-96-6
  • Cat. No. CS-D1537
  • Purity ≥98%
  • MDL No. MFCD00002260
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇ClO₂
  • Molecular Weight 158.58
  • Synonym(s) 65262-96-6
  • SMILES OC1=CC(OC)=CC(Cl)=C1

Description

3-Chloro-5-methoxyphenol features a phenolic hydroxyl group flanked by electron-withdrawing chlorine and electron-donating methoxy substituents, creating a uniquely polarized aromatic system. This structural motif enables direct participation in cross-coupling reactions and facilitates incorporation into bioactive scaffolds requiring balanced electronic properties. The compound exhibits enhanced solubility in organic solvents compared to unsubstituted phenols and maintains stability under standard bench conditions.

Application

3-Chloro-5-methoxyphenol serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to functionalized aromatic scaffolds. Its ortho-chloro and para-methoxy substituents provide predictable reactivity in palladium-catalyzed cross-coupling reactions and allow for selective derivatization via electrophilic substitution or nucleophilic displacement. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic campaigns requiring reliable functional group compatibility.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB; ASTEX THERAPEUTICS LTD. Patent: WO2007/149033 A1, 2007 ; Location in patent: Page/Page column 68-69 ; WO 2007/149033 A1
  • Route2

    References

    • Maleczka Jr., Robert E.; Shi, Feng; Holmes, Daniel; Smith III, Milton R. Journal of the American Chemical Society, 2003 , vol. 125, # 26 p. 7792 - 7793
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 125, # 26 p. 7792 - 7793

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   29.46
  • LogP   2.0542
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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