2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 347389-74-6
Cat. No. CS-W010958
Purity≥96%
MDL No.MFCD13182122

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2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W010958

Structure of 347389-74-6

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General Information

CAS No. 347389-74-6
Cat. No. CS-W010958
Purity ≥96%
MDL No. MFCD13182122
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₃BO₂
Molecular Weight 152.00
Synonym(s) Ethynylboronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C#C)O1

Description

2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane features a boronate ester group paired with a terminal alkyne, enabling direct coupling in palladium-catalyzed reactions. This bench-stable reagent integrates cleanly into click chemistry and Suzuki-Miyaura protocols, delivering efficient access to functionalized alkynyl architectures with minimal side reactions.

Application

2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron source for palladium-catalyzed coupling reactions. Its tetramethyl-substituted dioxaborolane ring enhances air and moisture stability while enabling efficient Suzuki-Miyaura cross-coupling with aryl, vinyl, and heteroaryl halides. The terminal alkyne functionality allows for direct incorporation into conjugated frameworks, facilitating the synthesis of functionalized alkynes and extended π-systems under mild conditions.

Synthesis

Route1
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  347389-74-6
References
- Kim, Mansuk; Lee, Daesung Organic Letters, 2005 , vol. 7, # 9 p. 1865 - 1868

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS02
Signal Word : Danger	UN#: 1325
Class : 4.1	Packing Group : Ⅲ
Hazard Statements : H226-H315-H319
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

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Computational Chemistry Data

TPSA 18.46
LogP 1.251
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Conjugation Chemistry/Click Chemistry Terminal Alkynes

Key Words

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2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 347389-74-6

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