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ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate

  • CAS No. 960116-27-2

  • Cat. No. CS-0036576
  • Purity≥95%
  • MDL No.None

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

ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate|CS-0036576

Structure of 960116-27-2

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General Information

  • CAS No. 960116-27-2
  • Cat. No. CS-0036576
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BO₄S
  • Molecular Weight 282.16
  • Synonym(s) Ethyl thiophene-2-boronic acid pinacol ester-4-carboxylate
  • SMILES CCOC(=O)C1=CSC(=C1)B2OC(C)(C)C(C)(C)O2

Description

Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane enhances stability and reactivity under standard conditions. This thiophene-based building block integrates readily into complex molecular architectures.

Application

Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety ensures excellent bench stability and functional group tolerance, enabling efficient coupling with aryl and vinyl halides under mild conditions. Its thiophene core facilitates access to conjugated systems relevant in materials science and medicinal chemistry, while the ester group permits further derivatization. Ideal for modular synthesis of biaryl and heteroaryl scaffolds.

Safety Information

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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   44.76
  • LogP   2.224
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   3

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