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CS-W001157 4
Total: USD 88.00

2,2-Dimethylbenzo[d][1,3]dioxole

  • CAS No. 14005-14-2

  • Cat. No. CS-0153772
  • Purity≥98%
  • MDL No.MFCD08061594

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

2,2-Dimethylbenzo[d][1,3]dioxole|CS-0153772

Structure of 14005-14-2

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General Information

  • CAS No. 14005-14-2
  • Cat. No. CS-0153772
  • Purity ≥98%
  • MDL No. MFCD08061594
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀O₂
  • Molecular Weight 150.17
  • Synonym(s) 2,2-Dimethyl-1,3-benzodioxole
  • SMILES CC1(C)OC2=CC=CC=C2O1

Description

2,2-Dimethylbenzo[d][1,3]dioxole features a rigid, electron-rich benzodioxole core with steric protection from the dimethyl substitution at the bridgehead position. This configuration enhances stability and modulates electronic properties, making it valuable in medicinal chemistry and materials synthesis.

Application

2,2-Dimethylbenzo[d][1,3]dioxole serves as a stable, bench-ready heterocyclic building block featuring a rigid fused ring system with excellent functional group tolerance. Its dimethyl substitution enhances solubility and metabolic stability while preserving reactivity in palladium-catalyzed cross-coupling processes. The structure functions effectively as a bioisostere for phenyl or pyridine moieties in medicinal chemistry and enables efficient incorporation into complex scaffolds via standard electrophilic functionalization or Suzuki-Miyaura coupling.

Synthesis

  • Route1
    • null|null
      120-80-9
    • null|null
      77-76-9
    • ~95%
    • In-stock
      2,2-Dimethylbenzo[d][1,3]dioxole|CS-0153772
      14005-14-2

    References

    • Meltzer, Peter C.; McPhee, Mark; Madras, Bertha K. Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 22 p. 4133 - 4137
  • Route2
    • null|null
      120-80-9
    • ~46%
    • In-stock
      2,2-Dimethylbenzo[d][1,3]dioxole|CS-0153772
      14005-14-2

    References

    • SHELL INTERNATIONALE RESEARCH, MAATSCHAPPIJ B.V. Patent: EP525877 A1, 1993 ;
  • Route3
    • null|null
      120-80-9
    • null|null
      67-64-1
    • ~96%
    • In-stock
      2,2-Dimethylbenzo[d][1,3]dioxole|CS-0153772
      14005-14-2

    References

    • Bikbulatov; Timofeeva; Zorina; Safiev; Zorin; Rakhmankulov Russian Journal of General Chemistry, 1996 , vol. 66, # 11 p. 1805 - 1806

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   18.46
  • LogP   2.1939
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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