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

Name: N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide
Brand: ChemScene
Availability: InStock
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CAS No. 486422-04-2
Cat. No. CS-0046873
Purity≥97%
MDL No.None

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N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide|CS-0046873

Structure of 486422-04-2

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General Information

CAS No. 486422-04-2
Cat. No. CS-0046873
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₂BNO₄S
Molecular Weight 311.20
Synonym(s) 4-(N,N-Dimethylaminosulfonyl)phenylboronic acid pinacol ester
SMILES O=S(C1=CC=C(B(OC2(C)C)OC2(C)C)C=C1)(N(C)C)=O

Description

N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide is a bench-stable boronate reagent featuring a sulfonamide handle and electron-rich boronate moiety. This compound integrates readily into Suzuki-Miyaura coupling reactions under mild conditions, enabling efficient C–C bond formation with aryl halides. The tetramethyl-substituted dioxaborolane enhances stability and solubility in common organic solvents.

Application

N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide serves as a stable, bench-ready boronate building block for Suzuki-Miyaura coupling reactions. The sulfonamide group provides excellent solubility and functional group tolerance, enabling efficient late-stage diversification in medicinal chemistry. Its tetramethylboronate moiety facilitates reliable cross-coupling under mild conditions, making it ideal for constructing biaryl scaffolds in drug discovery and materials science applications.

Synthesis

Route1
- In-stock
  
  707-60-8
- In-stock
  
  73183-34-3
- ~78%
- In-stock
  
  486422-04-2
References
- WO2004/9086 A1, ; Page/Page column 60 ; WO 2004/009086 A1
Route2
- In-stock
  
  22184-85-6
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  486422-04-2
References
- WO2006/4703 A2, ; Page/Page column 37-38 ; WO 2006/004703 A2

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 55.84
LogP 1.2361
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 486422-04-2

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