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7-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

  • CAS No. 912331-75-0

  • Cat. No. CS-0197500
  • Molecule weight261.10
  • Purity≥98%
  • MDL No.None

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

7-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|CS-0197500

Structure of 912331-75-0

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General Information

  • CAS No. 912331-75-0
  • Cat. No. CS-0197500
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₇BFNO₂
  • Molecular Weight 261.10
  • Synonym(s) 7-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole B
  • SMILES CC1(C)C(C)(C)OB(C(N2)=CC3=C2C(F)=CC=C3)O1

Description

7-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole delivers a fluorinated indole scaffold paired with a stable boronate ester for efficient cross-coupling. The tetramethyl-substituted dioxaborolane enhances shelf life and reactivity under standard conditions. This reagent integrates readily into Suzuki-Miyaura transformations, enabling rapid access to functionalized heterocycles in medicinal chemistry and materials synthesis.

Application

7-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables robust coupling with aryl and heteroaryl halides under mild conditions, while the 7-fluoro substituent enhances electrophilic reactivity in downstream transformations. Bench-stable and readily purified by flash chromatography, it facilitates efficient construction of complex indole-based scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • ELI LILLY AND COMPANY Patent: WO2006/107784 A1, 2006 ; Location in patent: Page/Page column 66 ; WO 2006/107784 A1

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   34.25
  • LogP   2.6062
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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