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CS-W001157 4
Total: USD 88.00

5-Bromo-2,3-dimethyl-1H-indole

  • CAS No. 4583-55-5

  • Cat. No. CS-0153594
  • Purity≥98%
  • MDL No.MFCD00850844

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

5-Bromo-2,3-dimethyl-1H-indole|CS-0153594

Structure of 4583-55-5

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General Information

  • CAS No. 4583-55-5
  • Cat. No. CS-0153594
  • Purity ≥98%
  • MDL No. MFCD00850844
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₀BrN
  • Molecular Weight 224.10
  • Synonym(s) 5-Bromo-2,3-dimethylindole
  • SMILES CC1=C(C)NC2=C1C=C(C=C2)Br

Description

5-Bromo-2,3-dimethyl-1H-indole is a halogenated indole scaffold featuring bromine at the 5-position and methyl groups flanking the 2- and 3-positions. This electron-deficient heterocycle integrates readily into complex molecular architectures, offering enhanced stability and defined regiochemistry for synthetic applications in medicinal chemistry and materials science.

Application

5-Bromo-2,3-dimethyl-1H-indole serves as a versatile building block for the synthesis of brominated indole scaffolds commonly found in pharmaceutical and agrochemical research. Its well-defined substitution pattern enables predictable regioselective functionalization via Pd-catalyzed cross-coupling reactions. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it ideal for use in iterative synthetic sequences and heterocycle construction workflows.

Synthesis

  • Route1
    • null|null
      1417407-56-7
    • ~82%
    • In-stock
      5-Bromo-2,3-dimethyl-1H-indole|CS-0153594
      4583-55-5

    References

    • Nguyen, Quyen; Nguyen, Tuyen; Driver, Tom G. Journal of the American Chemical Society, 2013 , vol. 135, # 2 p. 620 - 623
  • Route2
    • null|null
      598-30-1
    • In-stock
      4-Bromobenzenediazonium tetrafluoroborate|CS-0360317
      673-40-5
    • ~80%
    • In-stock
      5-Bromo-2,3-dimethyl-1H-indole|CS-0153594
      4583-55-5

    References

    • Zhang, Zhi-Guang; Haag, Benjamin A.; Li, Jin-Shan; Knochel, Paul Synthesis, 2011 , # 1 p. 23 - 29
  • Route3
    • In-stock
      (4-Bromophenyl)hydrazine hydrochloride|CS-W013083
      622-88-8
    • null|null
      78-93-3
    • ~77%
    • In-stock
      5-Bromo-2,3-dimethyl-1H-indole|CS-0153594
      4583-55-5

    References

    • Takemoto, Masumi; Iwakiri, Yasutaka; Tanaka, Kiyoshi Heterocycles, 2007 , vol. 72, p. 373 - 383

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   15.79
  • LogP   3.54724
  • H_Acceptors   0
  • H_Donors   1
  • Rotatable_Bonds   0

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