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Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-2-carboxylate

  • CAS No. 690632-26-9

  • Cat. No. CS-0369157
  • Purity≥97%
  • MDL No.None

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

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-2-carboxylate|CS-0369157

Structure of 690632-26-9

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General Information

  • CAS No. 690632-26-9
  • Cat. No. CS-0369157
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₁₉BO₄S
  • Molecular Weight 318.20
  • Synonym(s) Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzothiophene-2-carboxylate
  • SMILES O=C(C1=CC2=CC(B3OC(C)(C)C(C)(C)O3)=CC=C2S1)OC

Description

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-2-carboxylate integrates a boronate handle into a benzo[b]thiophene scaffold, enabling efficient Suzuki-Miyaura coupling. This bench-stable reagent features excellent functional group tolerance and moisture resistance, streamlining the synthesis of complex heteroaryl architectures in medicinal chemistry and materials science.

Application

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-2-carboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The boryl group enables efficient C–C bond formation under mild conditions, while the methyl ester and benzo[b]thiophene core provide orthogonal functional handles for further derivatization. Its bench-stable nature, high reactivity, and compatibility with diverse substrates make it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

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

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Computational Chemistry Data

  • TPSA   44.76
  • LogP   2.9871
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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