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CS-W001157 4
Total: USD 88.00

3-(Trifluoroacetyl)indole

  • CAS No. 14618-45-2

  • Cat. No. CS-0099181
  • Molecule weightNone
  • Purity≥97%
  • MDL No.MFCD00182114

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

3-(Trifluoroacetyl)indole|CS-0099181

Structure of 14618-45-2

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General Information

  • CAS No. 14618-45-2
  • Cat. No. CS-0099181
  • Purity ≥97%
  • MDL No. MFCD00182114
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆F₃NO
  • Molecular Weight None
  • Synonym(s) 2,2,2-trifluoro-1-(1H-indol-3-yl)ethan-1-one
  • SMILES O=C(C(F)(F)F)C1=CNC2=C1C=CC=C2

Description

3-(Trifluoroacetyl)indole features a strongly electron-withdrawing trifluoroacetyl group attached to the indole scaffold, enhancing electrophilicity at the 3-position. This substitution enables direct functionalization in cross-coupling and cyclization reactions, serving as a key intermediate in the synthesis of complex heterocycles and bioactive molecules under mild conditions.

Application

3-(Trifluoroacetyl)indole serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the indole C3 position. The trifluoroacetyl group provides enhanced electrophilicity for nucleophilic substitution and facilitates subsequent deprotection or transformation into diverse indole derivatives. Its bench stability and compatibility with standard reaction conditions make it well-suited for medicinal chemistry campaigns and heterocycle synthesis.

Synthesis

  • Route1
    • Indole, ≥99%|CS-1268948
      120-72-9
    • null|null
      407-25-0
    • ~87%
    • In-stock
      3-(Trifluoroacetyl)indole|CS-0099181
      14618-45-2

    References

    • Hassinger, Heidi L.; Soll, Richard M.; Gribble, Gordon W. Tetrahedron Letters, 1998 , vol. 39, # 20 p. 3095 - 3098
  • Route2
    • Indole, ≥99%|CS-1268948
      120-72-9
    • ~%
    • In-stock
      3-(Trifluoroacetyl)indole|CS-0099181
      14618-45-2

    References

    • US5994270 A1, ;
  • Route3
    • Indole, ≥99%|CS-1268948
      120-72-9
    • null|null
      407-25-0
    • ~20%
    • null|null
      62615-78-5
    • In-stock
      3-(Trifluoroacetyl)indole|CS-0099181
      14618-45-2
    • null|null
      82342-77-6

    References

    • Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), , p. 523 - 530

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   32.86
  • LogP   2.9129
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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