4-Nitrophenyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl carbonate

Name: 4-Nitrophenyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl carbonate
Brand: ChemScene
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CAS No. 1254765-89-3
Cat. No. CS-0650891
Purity≥97%
MDL No.None

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4-Nitrophenyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl carbonate|CS-0650891

Structure of 1254765-89-3

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Description

This boronate ester features a 4-nitrophenyl carbonate handle paired with a sterically hindered boryl group, enabling stable coupling under standard conditions. The para-nitro substituent enhances electrophilicity, facilitating efficient Suzuki-Miyaura cross-coupling reactions in synthetic workflows.

Application

4-Nitrophenyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl carbonate serves as a stable, bench-friendly boronate ester building block for Suzuki-Miyaura cross-coupling reactions. Its 4-nitrophenyl carbonate moiety enables mild, selective activation under basic conditions, facilitating efficient coupling with aryl halides and triflates. The tetramethyl-1,3,2-dioxaborolane group offers excellent functional group tolerance and stability, making it well-suited for iterative synthesis of biaryl scaffolds in medicinal chemistry and materials science applications.

General Information

CAS No. 1254765-89-3
Cat. No. CS-0650891
Purity ≥97%
MDL No. None
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₂BNO₇
Molecular Weight 399.20
Synonym(s) None
SMILES O=C(OCC1=CC=C(B2OC(C)(C(C)(C)O2)C)C=C1)OC3=CC=C([N+]([O-])=O)C=C3

Computational Chemistry Data

TPSA 97.13
LogP 3.6096
H_Acceptors 7
H_Donors 0
Rotatable_Bonds 5

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 : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

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Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Nitrophenyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl carbonate

CAS No. 1254765-89-3

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