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CS-W001157 4
Total: USD 88.00

5-Chloro-2,3-dihydrobenzofuran-3-amine

  • CAS No. 769-21-1

  • Cat. No. CS-0187129
  • Purity≥95%
  • MDL No.None

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

5-Chloro-2,3-dihydrobenzofuran-3-amine|CS-0187129

Structure of 769-21-1

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General Information

  • CAS No. 769-21-1
  • Cat. No. CS-0187129
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈ClNO
  • Molecular Weight 169.61
  • Synonym(s) 5-Chloro-2,3-dihydro-benzofuran-3-ylamine
  • SMILES C1=CC2=C(C=C1Cl)C(CO2)N

Description

This 5-chloro-2,3-dihydrobenzofuran-3-amine features a chlorinated dihydrobenzofuran core with a primary amine at the 3-position, offering enhanced solubility and reactivity in synthetic transformations. The electron-withdrawing chlorine substituent modulates electronic density, enabling selective coupling reactions in medicinal chemistry and materials science applications.

Application

5-Chloro-2,3-dihydrobenzofuran-3-amine serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles through palladium-catalyzed couplings and electrophilic functionalization. Its bench-stable structure features a reactive amine group with moderate nucleophilicity and excellent compatibility with common protecting groups. The chloro substituent facilitates downstream cross-coupling reactions, while the dihydrobenzofuran scaffold provides structural rigidity relevant to kinase inhibitor and CNS-targeted compound development.

Synthesis

  • Route1
    • 5-Chloro-2,3-dihydrobenzofuran-3-amine hydrochloride|CS-0200098
      669-45-4
    • ~97%
    • In-stock
      5-Chloro-2,3-dihydrobenzofuran-3-amine|CS-0187129
      769-21-1

    References

    • PFIZER INC.; AM ENDE, Christopher William; JOHNSON, Douglas Scott; O'DONNELL, Christopher John; PETTERSSON, Martin Youngjin; SUBRAMANYAM, Chakrapani Patent: WO2011/48525 A1, 2011 ; Location in patent: Page/Page column 49 ; WO 2011/048525 A1
  • Route2

    References

    • Turan-Zitouni, G.; Berge, G.; Noel-Artis, A. M.; Chevallet, P.; Fulcrand, P.; Castel, J. Farmaco, Edizione Scientifica, 1988 , vol. 43, # 7-8 p. 643 - 656
  • Route3

    References

    • PFIZER INC.; AM ENDE, Christopher William; JOHNSON, Douglas Scott; O'DONNELL, Christopher John; PETTERSSON, Martin Youngjin; SUBRAMANYAM, Chakrapani Patent: WO2011/48525 A1, 2011 ; WO 2011/048525 A1

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   35.25
  • LogP   1.7322
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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