(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane

Name: (E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane
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CAS No. 480425-30-7
Cat. No. CS-0154943
Molecule weight312.33
Purity≥97%
MDL No.MFCD05664265

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(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane|CS-0154943

Structure of 480425-30-7

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General Information

CAS No. 480425-30-7
Cat. No. CS-0154943
Purity ≥97%
MDL No. MFCD05664265
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₃₃BO₃Si
Molecular Weight 312.33
Synonym(s) None
SMILES C(=C/CCO[Si](C(C)(C)C)(C)C)\B1OC(C)(C)C(C)(C)O1

Description

This boronate ester features a (E)-configured butenyl linker with a tert-butyldimethylsilyl-protected oxygen, enabling stable, selective coupling in palladium-catalyzed cross-coupling reactions. The tetramethyl-1,3,2-dioxaborolane moiety delivers high reactivity and compatibility under standard conditions.

Application

(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane serves as a stable, bench-ready boronate ester enabling efficient Suzuki-Miyaura coupling reactions. The (E)-configured vinyl boronate facilitates stereoselective C–C bond formation with aryl and vinyl halides, offering high functional group tolerance and compatibility with diverse reaction conditions. Its robustness under standard handling and straightforward purification make it a practical choice for constructing complex molecular architectures in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  78592-82-2
- 25015-63-8
- ~91%
- In-stock
  
  480425-30-7
References
- Wang, Yanong D.; Kimball, Gregory; Prashad, Amar S.; Wang, Yan Tetrahedron Letters, 2005 , vol. 46, # 50 p. 8777 - 8780
Route2
- In-stock
  
  78592-82-2
- 25015-63-8
- ~%
- 116376-35-3
- In-stock
  
  480425-30-7
References
- Wyeth Patent: US2006/281943 A1, 2006 ; Location in patent: Page/Page column 2 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS07
Signal Word : Danger	UN#: 3265
Class : 8	Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 27.69
LogP 4.5859
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Organosilicon compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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(E)-tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxy)silane

CAS No. 480425-30-7

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