4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane
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CAS No. 190788-59-1
Cat. No. CS-W000891
Purity≥97%
MDL No.MFCD02179447

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4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane|CS-W000891

Structure of 190788-59-1

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General Information

CAS No. 190788-59-1
Cat. No. CS-W000891
Purity ≥97%
MDL No. MFCD02179447
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₆BNO₄
Molecular Weight 249.07
Synonym(s) 2-Nitrophenylboronic Acid Pinacol Ester
SMILES O=[N+](C1=CC=CC=C1B2OC(C)(C)C(C)(C)O2)[O-]

Description

This boronate ester features a nitro-substituted aryl group and tetramethyl substitution, delivering enhanced stability and reactivity in Suzuki-Miyaura coupling. The electron-deficient nitrophenyl moiety enables efficient cross-coupling under standard conditions, while the dioxaborolane scaffold ensures bench-stable handling and minimal protodeboronation.

Application

4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent enabling efficient Suzuki-Miyaura cross-coupling reactions. Its ortho-nitroaryl group facilitates directed metalation and enhances regioselectivity in heterocyclic synthesis. The tetramethyl-substituted dioxaborolane core ensures excellent air and moisture stability, simplifying handling and purification. Functions reliably in diverse reaction conditions, supporting scalable synthesis of complex biaryls and functionalized aromatic scaffolds.

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

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Computational Chemistry Data

TPSA 61.6
LogP 1.894
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane

CAS No. 190788-59-1

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