Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane

Name: Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane
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CAS No. 159087-46-4
Cat. No. CS-W000113
Purity≥95%
MDL No.MFCD13182130

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane|CS-W000113

Structure of 159087-46-4

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General Information

CAS No. 159087-46-4
Cat. No. CS-W000113
Purity ≥95%
MDL No. MFCD13182130
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₁BO₂Si
Molecular Weight 224.18
Synonym(s) trimethyl-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl]silane
SMILES C[Si](C#CB1OC(C(O1)(C)C)(C)C)(C)C

Description

Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane features a boronate-protected alkyne moiety flanked by a stable dioxaborolane ring and a trimethylsilyl group. This combination delivers enhanced stability and compatibility with palladium-catalyzed coupling reactions under standard conditions. The silyl-protected alkyne enables orthogonal functionalization in complex synthesis workflows.

Application

Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane serves as a stable, bench-ready building block for Sonogashira coupling reactions. Its boronate ester and silyl acetylene functionalities enable efficient cross-coupling with aryl and vinyl halides under palladium catalysis, facilitating rapid access to conjugated enynes and alkyne-containing scaffolds. The molecule exhibits excellent functional group tolerance, minimal protodeboronation, and straightforward purification, making it ideal for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

Route1
- 61676-62-8
- 1066-54-2
- ~63%
- In-stock
  
  159087-46-4
References
- Harker, Wesley R.R.; Delaney, Patrick M.; Simms, Michael; Tozer, Matthew J.; Harrity, Joseph P.A. Tetrahedron, 2013 , vol. 69, # 5 p. 1546 - 1552
Route2
- 25015-63-8
- 1066-54-2
- ~85%
- In-stock
  
  159087-46-4
References
- Lee, Chun-I; Zhou, Jia; Ozerov, Oleg V. Journal of the American Chemical Society, 2013 , vol. 135, # 9 p. 3560 - 3566

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 2.4986
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Organosilicon compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane

CAS No. 159087-46-4

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