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CS-W001157 4
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N-(Benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide

  • CAS No. 227199-07-7

  • Cat. No. CS-0131274
  • Purity≥97%
  • MDL No.MFCD00245737

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

N-(Benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide|CS-0131274

Structure of 227199-07-7

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General Information

  • CAS No. 227199-07-7
  • Cat. No. CS-0131274
  • Purity ≥97%
  • MDL No. MFCD00245737
  • Storage 4°C, stored under nitrogen, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈ClNO₃
  • Molecular Weight 213.62
  • Synonym(s) N-(1,3-benzodioxol-5-yl)-2-chloroacetamide
  • SMILES O=C(NC1=CC=C(OCO2)C2=C1)CCl

Description

N-(Benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide features a benzodioxole moiety linked to a chloroacetamide group, enabling efficient incorporation into bioconjugation workflows. This bench-stable reagent offers enhanced solubility in polar solvents and facilitates selective coupling under mild conditions.

Application

N-(Benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide serves as a versatile building block in medicinal chemistry, enabling efficient access to bioactive heterocycles through nucleophilic substitution and cyclization reactions. Its benzo[d][1,3]dioxole moiety imparts metabolic stability and favorable lipophilicity, while the 2-chloroacetamide group provides a reactive handle for conjugation and scaffold elaboration. Bench-stable and readily purified by flash chromatography, it functions effectively in standard amide coupling and cycloaddition protocols.

Synthesis

  • Route1
    • null|null
      14268-66-7
    • null|null
      79-04-9
    • ~74%
    • In-stock
      N-(Benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide|CS-0131274
      227199-07-7

    References

    • Baraldi, Pier Giovanni; Preti, Delia; Tabrizi, Mojgan Aghazadeh; Fruttarolo, Francesca; Saponaro, Giulia; Baraldi, Stefania; Romagnoli, Romeo; Moorman, Allan R.; Gessi, Stefania; Varani, Katia; Borea, Pier Andrea Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 7 p. 2514 - 2527
  • Route2
    • null|null
      14268-66-7
    • ~90%
    • In-stock
      N-(Benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide|CS-0131274
      227199-07-7

    References

    • Bhatia, Pramila A.; Daanen, Jerome F.; Hakeem, Ahmed A.; Kolasa, Teodozyj; Matulenko, Mark A.; Mortell, Kathleen H.; Patel, Meena V.; Stewart, Andrew O.; Wang, Xueqing; Xia, Zhiren; Zhang, Henry Q. Patent: US2004/29887 A1, 2004 ;
  • Route3
    • null|null
      79-04-9
    • ~%
    • In-stock
      N-(Benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide|CS-0131274
      227199-07-7

    References

    • Journal of the American Chemical Society, , vol. 41, p. 1457

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

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Computational Chemistry Data

  • TPSA   47.56
  • LogP   1.5926
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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