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Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

  • CAS No. 1198605-53-6

  • Cat. No. CS-0040767
  • Molecule weight251.09
  • Purity≥97%
  • MDL No.MFCD16995409

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

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate|CS-0040767

Structure of 1198605-53-6

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General Information

  • CAS No. 1198605-53-6
  • Cat. No. CS-0040767
  • Purity ≥97%
  • MDL No. MFCD16995409
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₈BNO₄
  • Molecular Weight 251.09
  • Synonym(s) None
  • SMILES O=C(C1=CC(B2OC(C)(C)C(C)(C)O2)=CN1)OC

Description

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate features a boronate ester group enabling reliable Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane enhances stability and shelf life. This bench-stable reagent integrates efficiently into complex molecular architectures, particularly in the synthesis of functionalized heterocycles and bioactive compounds.

Application

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety enables efficient coupling with aryl and vinyl halides under mild conditions, while the pyrrole core provides a versatile scaffold for medicinal chemistry and materials synthesis. Its high functional group tolerance and ease of purification make it ideal for iterative C–C bond formation in complex molecule assembly.

Synthesis

  • Route1

    References

    • OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W. Patent: WO2012/74951 A1, 2012 ; Location in patent: Page/Page column 101 ; WO 2012/074951 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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   60.55
  • LogP   1.1005
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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