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

Name: N-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
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CAS No. 943911-67-9
Cat. No. CS-0178683
Purity≥98%
MDL No.None

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N-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide|CS-0178683

Structure of 943911-67-9

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General Information

CAS No. 943911-67-9
Cat. No. CS-0178683
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₂BNO₃
Molecular Weight 275.15
Synonym(s) 3-(N-Ethylaminocarbonyl)phenylboronic acid pinacol ester
SMILES O=C(NCC)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1

Description

N-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety enhances stability and shelf life under ambient conditions. This bench-stable reagent integrates readily into synthetic sequences for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Application

N-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. Its stable boronate ester group enables efficient C–C bond formation under mild conditions, with excellent functional group tolerance and bench stability. The N-ethyl amide moiety enhances solubility and modulates reactivity, facilitating integration into complex molecular architectures. This compound functions reliably in the synthesis of biaryl scaffolds and pharmaceutical intermediates.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H317-H319
Precautionary Statements : P261-P264-P272-P280-P302+P352-P362+P364-P501

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Computational Chemistry Data

TPSA 47.56
LogP 1.7355
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Amide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 943911-67-9

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