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N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

  • CAS No. 486422-05-3

  • Cat. No. CS-0100023
  • Purity≥97%
  • MDL No.MFCD07368237

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

N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide|CS-0100023

Structure of 486422-05-3

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General Information

  • CAS No. 486422-05-3
  • Cat. No. CS-0100023
  • Purity ≥97%
  • MDL No. MFCD07368237
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₂BNO₄S
  • Molecular Weight 311.20
  • Synonym(s) 3-(N,N-DIMETHYLSULFAMOYL)PHENYLBORONIC ACID, PINACOL ESTER
  • SMILES O=S(C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1)(N(C)C)=O

Description

N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide features a boronate ester group integrated with a sulfonamide moiety, enabling efficient cross-coupling under mild conditions. The tetramethyl-substituted dioxaborolane enhances stability and solubility in organic media. This compound serves as a robust building block for constructing functionalized aryl scaffolds in medicinal chemistry and materials science applications.

Application

N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The sulfonamide group provides enhanced solubility and functional group tolerance, while the tetramethyl-substituted dioxaborolane ensures high reactivity and minimal protodeboronation. It facilitates efficient C–C bond formation under mild conditions, enabling streamlined synthesis of biaryl scaffolds and functionalized heterocycles 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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   55.84
  • LogP   1.2361
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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