2-(5-Bromo-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(5-Bromo-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 868629-78-1
Cat. No. CS-0173931
Purity≥98%
MDL No.None

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2-(5-Bromo-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0173931

Structure of 868629-78-1

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General Information

CAS No. 868629-78-1
Cat. No. CS-0173931
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₈BBrO₃
Molecular Weight 313.00
Synonym(s) 5-Bromo-2-methoxyphenylboronic acid pinacol ester
SMILES CC1(C(C)(OB(O1)C2=C(OC)C=CC(Br)=C2)C)C

Description

This boronate reagent features a bromo-substituted methoxyaryl group, enabling efficient coupling in palladium-catalyzed cross-coupling reactions. The tetramethyl-dioxaborolane moiety provides enhanced stability and shelf-life under ambient conditions. Designed for reliable performance in Suzuki-Miyaura transformations, it integrates seamlessly into complex molecular architectures with minimal handling requirements.

Application

2-(5-Bromo-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a reliable boron building block for Suzuki-Miyaura cross-coupling reactions. The bromo group enables efficient palladium-catalyzed coupling with aryl and heteroaryl halides, while the pinacol boronate moiety offers excellent stability, ease of handling, and compatibility with diverse functional groups. Its methoxy-substituted aryl framework provides a versatile scaffold for constructing complex biaryl systems in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  190788-60-4
- ~91%
- In-stock
  
  868629-78-1
References
- Qiu, Di; Mo, Fanyang; Zheng, Zhitong; Zhang, Yan; Wang, Jianbo Organic Letters, 2010 , vol. 12, # 23 p. 5474 - 5477

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

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Computational Chemistry Data

TPSA 27.69
LogP 2.7569
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-(5-Bromo-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 868629-78-1

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