N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

Name: N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 305448-92-4
Cat. No. CS-0154957
Purity≥97%
MDL No.MFCD05663881

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N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide|CS-0154957

Structure of 305448-92-4

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General Information

CAS No. 305448-92-4
Cat. No. CS-0154957
Purity ≥97%
MDL No. MFCD05663881
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₄S
Molecular Weight 297.18
Synonym(s) N-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYLMETHANESULFONAMIDE
SMILES CS(=O)(NC1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1)=O

Description

N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide features a boronate ester group flanked by tetramethyl-substituted dioxaborolane rings, enabling stable coupling in Suzuki-Miyaura reactions. The methanesulfonamide moiety provides enhanced solubility and metabolic stability. This compound serves as a key building block for bioactive molecule synthesis.

Application

N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions, offering excellent functional group tolerance and bench stability. Its methanesulfonamide handle provides a polar, robust amine surrogate suitable for downstream derivatization in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  83922-51-4
- In-stock
  
  73183-34-3
- ~92%
- In-stock
  
  305448-92-4
References
- AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UM PHARMAUJI SDN. BHD; GUMMADI, Venkateshwar, Rao; HOSAHALLI, Subramanya; NANDURI, Srinivas; AGGUNDA RENUKAPPA, Girish Patent: WO2014/6554 A1, 2014 ; Location in patent: Page/Page column 28 ;
Route2
- 124-63-0
- In-stock
  
  210907-84-9
- ~81%
- In-stock
  
  305448-92-4
References
- Kressierer, Christoph J.; Lehnemann, Bernd; Jung, Jorg Patent: US2008/269523 A1, 2008 ; Location in patent: Page/Page column 6 ;
Route3
- 54769-22-1
- In-stock
  
  210907-84-9
- ~16%
- In-stock
  
  305448-92-4
References
- Davison, Joshua Zwick; Jones, Winton Dennis; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael Patent: US2003/225266 A1, 2003 ; Location in patent: Page 24 ;

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

Quality Control

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Computational Chemistry Data

TPSA 64.63
LogP 1.3573
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

CAS No. 305448-92-4

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