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

Name: (E)-2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
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CAS No. 223919-54-8
Cat. No. CS-W014056
Purity≥98%
MDL No.MFCD15144834

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(E)-2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W014056

Structure of 223919-54-8

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General Information

CAS No. 223919-54-8
Cat. No. CS-W014056
Purity ≥98%
MDL No. MFCD15144834
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BClO₂
Molecular Weight 264.56
Synonym(s) Trans-2 - (4-chlorophenyl) vinylboric acid pinacol ester
SMILES ClC1=CC=C(C=C1)/C=C/B(OC2(C)C)OC2(C)C

Description

(E)-2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a bench-stable boronate reagent featuring a stereodefined (E)-vinyl chloride moiety. This configuration enables efficient palladium-catalyzed cross-coupling reactions with aryl halides and triflates. The tetramethyl-substituted dioxaborolane ring enhances stability and solubility in organic solvents. Designed for use in late-stage functionalization and diversity-oriented synthesis, the compound delivers high yields under mild reaction conditions.

Application

(E)-2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for palladium-catalyzed cross-coupling reactions. The (E)-configured vinylboronate enables efficient Suzuki-Miyaura coupling with aryl halides and pseudohalides, offering high regioselectivity and functional group tolerance. Its tetramethyl-substituted dioxaborolane ring enhances stability and simplifies purification, making it ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  873-73-4
- In-stock
  
  73183-34-3
- ~85%
- In-stock
  
  223919-54-8
References
- Zhao, Jie; Niu, Zhiqiang; Fu, Hua; Li, Yadong Chemical Communications, 2014 , vol. 50, # 16 p. 2058 - 2060
Route2
- In-stock
  
  76-09-5
- In-stock
  
  154230-29-2
- ~88%
- In-stock
  
  223919-54-8
References
- Koolmeister, Tobias; Soedergren, Mikael; Scobie, Martin Tetrahedron Letters, 2002 , vol. 43, # 34 p. 5965 - 5968

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 3.9846
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 223919-54-8

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