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tert-Butyl (3-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)carbamate

  • CAS No. 2649788-76-9

  • Cat. No. CS-0372984
  • Molecule weight400.30
  • Purity≥96%
  • MDL No.None

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

tert-Butyl (3-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)carbamate|CS-0372984

Structure of 2649788-76-9

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General Information

  • CAS No. 2649788-76-9
  • Cat. No. CS-0372984
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₂₅BN₂O₄S
  • Molecular Weight 400.30
  • Synonym(s) None
  • SMILES N#CC1=C(NC(OC(C)(C)C)=O)SC2=CC=CC(B3OC(C)(C(C)(C)O3)C)=C12

Description

tert-Butyl (3-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)carbamate features a boronate ester group enabling robust Suzuki-Miyaura coupling under standard conditions. The molecule integrates a cyano substituent and a bench-stable carbamate protecting group, offering enhanced solubility and stability during synthetic workflows. This compound serves as a key building block for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Application

tert-Butyl (3-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)carbamate serves as a versatile boron-containing building block for Suzuki-Miyaura coupling reactions. The dioxaborolane moiety enables stable, room-temperature handling and efficient cross-coupling with aryl halides and pseudohalides. The cyano group enhances electronic modulation and facilitates downstream transformations, while the Boc carbamate provides orthogonal protection. This compound functions reliably in the synthesis of complex heterocyclic scaffolds relevant to medicinal chemistry and materials science.

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   80.58
  • LogP   4.41918
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   2

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