(E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: (E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 1242770-51-9
Cat. No. CS-0438156
Purity≥96%
MDL No.None

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(E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0438156

Structure of 1242770-51-9

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General Information

CAS No. 1242770-51-9
Cat. No. CS-0438156
Purity ≥96%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BBrO₂
Molecular Weight 309.01
Synonym(s) (E)-(4-bromostyryl)boronic acid pinacol ester
SMILES BrC(C=C1)=CC=C1/C=C/B2OC(C)(C(C)(O2)C)C

Description

(E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a bench-stable boronate ester featuring a stereodefined vinyl-boronate linkage. This reagent integrates seamlessly into cross-coupling reactions, enabling efficient access to substituted stilbenes and conjugated systems under mild conditions. The tetramethyl dioxaborolane moiety enhances stability and solubility in organic media.

Application

(E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for palladium-catalyzed cross-coupling reactions. It enables efficient Suzuki-Miyaura coupling with aryl halides and triflates, facilitating the construction of biaryl scaffolds under mild conditions. The (E)-configured vinylboronate exhibits high stereoselectivity and functional group tolerance, making it ideal for modular synthesis of complex molecules in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  766-96-1
- 25015-63-8
- ~86%
- In-stock
  
  1242770-51-9
References
- Yasu, Yusuke; Koike, Takashi; Akita, Munetaka Chemical Communications, 2013 , vol. 49, # 20 p. 2037 - 2039

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 4.0937
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(E)-2-(4-Bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 1242770-51-9

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