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5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole

  • CAS No. 53388-86-6

  • Cat. No. CS-0054222
  • Purity≥97%
  • MDL No.None

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

5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole|CS-0054222

Structure of 53388-86-6

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General Information

  • CAS No. 53388-86-6
  • Cat. No. CS-0054222
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂BrN
  • Molecular Weight 226.11
  • Synonym(s) 5-Bromo-3,3-dimethylindoline
  • SMILES CC1(C)CNC2=C1C=C(Br)C=C2

Description

This 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole features a brominated indole core with a sterically shielded dimethyl substitution at the 3-position, enhancing stability and directing electrophilic reactions selectively. The saturated C2–C3 bond enables controlled reactivity in transition metal-catalyzed couplings. This scaffold integrates readily into bioactive molecules requiring halogenated aromatic motifs.

Application

5-Bromo-3,3-dimethyl-2,3-dihydro-1H-indole serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo substituent. The 3,3-dimethyl substitution enhances steric protection and bench stability, while the dihydroindole core facilitates integration into heterocyclic scaffolds. Its functional group tolerance supports efficient derivatization in multi-step syntheses.

Synthesis

  • Route1

    References

    • American Home Products Corporation; Ligand Pharmaceuticals, Inc. Patent: US6329416 B1, 2001 ; US 6329416 B1
  • Route2
    • null|null
      866364-70-7
    • ~51%
    • In-stock
      5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole|CS-0054222
      53388-86-6

    References

    • CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang Patent: WO2014/89324 A1, 2014 ; Location in patent: Paragraph 0206 ;
  • Route3
    • null|null
      78-84-2
    • In-stock
      (4-Bromophenyl)hydrazine|CS-0060253
      589-21-9
    • ~55%
    • In-stock
      5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole|CS-0054222
      53388-86-6

    References

    • BAYER HEALTHCARE AG Patent: WO2005/19169 A2, 2005 ; Location in patent: Page/Page column 30; 31 ;

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   12.03
  • LogP   3.1522
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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