N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Name: N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 214360-57-3
Cat. No. CS-0041345
Purity≥95%
MDL No.MFCD06795690

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N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide|CS-0041345

Structure of 214360-57-3

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General Information

CAS No. 214360-57-3
Cat. No. CS-0041345
Purity ≥95%
MDL No. MFCD06795690
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₀BNO₃
Molecular Weight 261.12
Synonym(s) N-Methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide
SMILES CNC(=O)C1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1

Description

N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide features a boronate ester group flanked by electron-rich tetramethylcyclopentadienone rings, enabling robust coupling in Suzuki-Miyaura reactions. The N-methyl amide moiety enhances solubility and metabolic stability, while the bench-stable boronate resists hydrolysis under standard conditions. This compound integrates efficiently into complex molecular architectures with minimal side reactivity.

Application

N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. Its stability under ambient conditions and tolerance to diverse functional groups enable efficient construction of biaryl scaffolds in medicinal chemistry and materials synthesis. The N-methyl amide moiety enhances solubility and metabolic stability, while the tetramethyl-substituted dioxaborolane ensures high reactivity and low protodeboronation.

Synthesis

Route1
- In-stock
  
  27466-83-7
- In-stock
  
  73183-34-3
- ~93%
- In-stock
  
  214360-57-3
References
- GENZYME CORPORATION; BOURQUE, Elyse; CABRERA-SALAZAR, Mario, A.; CELATKA, Cassandra; CHENG, Seng, H.; HIRTH, Bradford; GOOD, Andrew; JANCSICS, Katherine; MARSHALL, John; METZ, Markus; SCHEULE, Ronald, K.; SKERLJ, Renato; XIANG, Yibin; ZHAO, Zhong; LEONARD, John; NATOLI, Thomas; MAKINO, Elina; HUSSON, Herve; BESKROVNAYA, Oxana Patent: WO2014/43068 A1, 2014 ; Location in patent: Page/Page column 267; 268 ;
Route2
- 124-40-3
- In-stock
  
  180516-87-4
- ~%
- In-stock
  
  214360-57-3
References
- WO2006/4703 A2, ; Page/Page column 50 ; WO 2006/004703 A2
Route3
- 74-89-5
- In-stock
  
  380499-68-3
- ~%
- In-stock
  
  214360-57-3
References
- US6639107 B1, ; Page/Page column 32 ;

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

Quality Control

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Computational Chemistry Data

TPSA 47.56
LogP 1.3454
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

CAS No. 214360-57-3

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