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

  • CAS No. 1040281-86-4

  • Cat. No. CS-0061103
  • Purity≥98%
  • 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)thiophene-3-carboxylate|CS-0061103

Structure of 1040281-86-4

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General Information

  • CAS No. 1040281-86-4
  • Cat. No. CS-0061103
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₇BO₄S
  • Molecular Weight 268.14
  • Synonym(s) 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-3-carboxylic acid methyl ester
  • SMILES CC1(C)C(C)(C)OB(C2=CC(=CS2)C(=O)OC)O1

Description

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylate features a boronate ester group flanked by sterically protected tetramethylcyclopentadienone moieties, enabling stable coupling in Suzuki-Miyaura reactions. The thiophene core provides electron-rich character, while the methyl ester facilitates downstream derivatization. This bench-stable reagent integrates efficiently into complex molecule synthesis under standard conditions.

Application

Methyl 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. Its stable tetramethylboronate group enables efficient C–C bond formation under mild conditions, with excellent functional group tolerance and bench stability. The methyl ester facilitates downstream derivatization, making it ideal for constructing thiophene-based heterocycles in medicinal chemistry and materials science applications.

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   44.76
  • LogP   1.8339
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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