4-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Name: 4-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
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CAS No. 863868-23-9
Cat. No. CS-0368943
Purity≥97%
MDL No.None

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4-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile|CS-0368943

Structure of 863868-23-9

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General Information

CAS No. 863868-23-9
Cat. No. CS-0368943
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BNO₃
Molecular Weight 259.11
Synonym(s) None
SMILES N#CC1=CC=C(OC)C=C1B2OC(C)(C)C(C)(C)O2

Description

4-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile delivers a boronate handle flanked by electron-rich methoxy and electron-deficient nitrile groups, enabling selective cross-coupling under mild conditions. This bench-stable reagent integrates readily into Suzuki-Miyaura reactions, pairing efficiently with aryl halides to construct complex biaryl architectures with high functional group tolerance.

Application

4-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The nitrile and methoxy groups provide orthogonal reactivity and enhanced solubility, while the stable pinacol boronate moiety enables efficient coupling under mild conditions. Ideal for constructing biaryl motifs in pharmaceutical and agrochemical synthesis, it offers excellent bench stability, straightforward purification, and compatibility with diverse reaction partners.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 51.48
LogP 1.86608
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

CAS No. 863868-23-9

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