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4,5-Dichloro-1H-indole

  • CAS No. 122509-73-3

  • Cat. No. CS-0096446
  • Molecule weight186.04
  • Purity≥95%
  • MDL No.MFCD16610777

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

4,5-Dichloro-1H-indole|CS-0096446

Structure of 122509-73-3

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General Information

  • CAS No. 122509-73-3
  • Cat. No. CS-0096446
  • Purity ≥95%
  • MDL No. MFCD16610777
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅Cl₂N
  • Molecular Weight 186.04
  • Synonym(s) 4,5-Dichloroindole
  • SMILES ClC1=C(Cl)C2=C(NC=C2)C=C1

Description

4,5-Dichloro-1H-indole features a rigid, electron-deficient indole core with chlorines at the 4 and 5 positions, enhancing its utility in heterocyclic synthesis. This bench-stable derivative integrates readily into pharmaceutical scaffolds and serves as a key intermediate in constructing bioactive molecules via cross-coupling and electrophilic substitution reactions.

Application

4,5-Dichloro-1H-indole serves as a valuable building block for the synthesis of biologically active heterocycles and pharmaceutical intermediates. The dichloro substitution pattern enhances electrophilic reactivity at C4 and C5, enabling straightforward functionalization via palladium-catalyzed coupling reactions. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Bromidge, Steven M.; Dabbs, Steven; Davies, David T.; Duckworth, D. Malcolm; Forbes, Ian T.; Ham, Peter; Jones, Graham E.; King, Frank D.; Saunders, Damian V.; Starr, Susannah; Thewlis, Kevin M.; Wyman, Paul A.; Blaney, Frank E.; Naylor, Christopher B.; Bailey, Fiona; Blackburn, Thomas P.; Holland, Vicky; Kennett, Guy A.; Riley, Graham J.; Wood, Martyn D. Journal of Medicinal Chemistry, 1998 , vol. 41, # 10 p. 1598 - 1612

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   15.79
  • LogP   3.4747
  • H_Acceptors   0
  • H_Donors   1
  • Rotatable_Bonds   0

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