5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one
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CAS No. 710348-69-9
Cat. No. CS-0097961
Purity≥95%
MDL No.MFCD09260491

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one|CS-0097961

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General Information

CAS No. 710348-69-9
Cat. No. CS-0097961
Purity ≥95%
MDL No. MFCD09260491
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BN₂O₃
Molecular Weight None
Synonym(s) 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one
SMILES O=C1NC2=CC=C(C=C2N1)B3OC(C)(C(C)(O3)C)C

Description

This boronate-functionalized benzoimidazolone integrates readily into Suzuki-Miyaura coupling reactions under standard conditions. The tetramethylboronate moiety enhances stability and solubility, enabling efficient cross-coupling with aryl halides. This bench-stable reagent streamlines the synthesis of biaryl-linked heterocycles for medicinal chemistry applications.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The stable boronate ester group enables efficient C–C bond formation under mild conditions, while the benzo[d]imidazol-2-one scaffold provides a rigid, electron-deficient heterocyclic core with favorable solubility and bench stability. Functions reliably in diverse synthetic workflows, including late-stage functionalization and library synthesis.

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 : 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 67.11
LogP 1.1554
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Key Words

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

CAS No. 710348-69-9

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