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5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole

  • CAS No. 476473-97-9

  • Cat. No. CS-0050761
  • Purity≥98%
  • MDL No.None

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

5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole|CS-0050761

Structure of 476473-97-9

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General Information

  • CAS No. 476473-97-9
  • Cat. No. CS-0050761
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅ClF₂O₂
  • Molecular Weight 206.57
  • Synonym(s) 5-ChloroMethyl-2,2-difluoro-benzo[1,3]dioxole
  • SMILES FC1(F)OC2=CC=C(CCl)C=C2O1

Description

5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole features a reactive chloromethyl group flanked by two fluorine atoms on the benzene ring, enhancing electrophilicity and metabolic stability. This difluorinated scaffold integrates readily into bioactive molecules, enabling efficient coupling in late-stage functionalization workflows under mild conditions.

Application

5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole serves as a versatile electrophilic building block for C–C and C–heteroatom coupling reactions. The chloromethyl group enables efficient functionalization via nucleophilic substitution, while the 2,2-difluorinated benzo[d][1,3]dioxole core provides enhanced metabolic stability and favorable lipophilicity. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for medicinal chemistry campaigns targeting CNS-active compounds and kinase inhibitors.

Synthesis

  • Route1

    References

    • VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2009/73757 A1, 2009 ; Location in patent: Page/Page column 20 ;
  • Route2
    • In-stock
      (2,2-Difluorobenzo[d][1,3]dioxol-5-yl)methanol|CS-M2545
      72768-97-9
    • null|null
      1634-04-4
    • ~%
    • In-stock
      5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole|CS-0050761
      476473-97-9

    References

    • VERTEX PHARMACEUTICALS INCORPORATED Patent: US2012/46330 A1, 2012 ; US 20120046330 A1
  • Route3

    References

    • VERTEX PHARMACEUTICALS INCORPORATED; KESHAVARZ-SHOKRI, Ali; ZHANG, Beili; ALCACIO, Tim, Edward; LEE, Elaine, Chungmin; ZHANG, Yuegang; KRAWIEC, Mariusz Patent: WO2011/119984 A1, 2011 ; WO 2011/119984 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H314-H335
Precautionary Statements : P233-P261-P270-P280-P302+P352-P304+P340-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.7469
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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