Description

4,4,5,5-Tetramethyl-2-[(2E)-3-(Trimethylsilyl)-2-propen-1-yl]-1,3,2-dioxaborolane is a high-value organoboron building block featuring a vinylsilane-substituted pinacol boronic ester. This compound matters for its dual functionality, offering both a protected boronic acid group and a silyl-protected alkene, which enables sequential cross-coupling and functionalization strategies in complex molecule synthesis. It is primarily needed by R&D chemists and process development scientists in the pharmaceutical, agrochemical, and advanced materials industries for constructing novel molecular architectures.

Application

• Suzuki-Miyaura Cross-Coupling Reactions: Serves as a key reagent for introducing the boronic ester moiety into target molecules for carbon-carbon bond formation.
• Sequential Functionalization: The vinylsilane group allows for subsequent Hiyama-type cross-coupling or other transformations after the initial boron-based coupling.
• Pharmaceutical Intermediate Synthesis: Used in the research and development of active pharmaceutical ingredients (APIs) and complex bioactive molecules.
• Agrochemical Compound Development: Applied in creating novel herbicides, fungicides, and insecticides with specific structural motifs.
• Materials Science Research: Employed in the synthesis of organic semiconductors, liquid crystals, and polymers with tailored electronic properties.
• Chemical Biology Probes: Useful for labeling and modifying biomolecules due to its orthogonal reactivity.

Basic Information

Product Name	4,4,5,5-Tetramethyl-2-[(2E)-3-(trimethylsilyl)-2-propen-1-yl]-1,3,2-dioxaborolane
CAS No.	79309-68-5
Molecular Formula	C₁₄H₂₉BO₂Si
Molecular Weight	268.28 g/mol
Synonyms	(2E)-3-(Trimethylsilyl)allylboronic acid pinacol ester; 2-[(2E)-3-(Trimethylsilyl)prop-2-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; (E)-3-(Trimethylsilyl)allylboronic acid pinacol ester; (E)-3-(Trimethylsilyl)-2-propen-1-ylboronic acid pinacol ester; Vinylsilane-substituted pinacol boronate; TMS-allylBPin; (E)-TMS-allylBPin
EINECS	Contact for details

Quality Control

Our 4,4,5,5-Tetramethyl-2-[(2E)-3-(trimethylsilyl)-2-propen-1-yl]-1,3,2-dioxaborolane is manufactured under strict quality management systems. Each batch undergoes rigorous analytical testing, including NMR, HPLC, and GC analysis, to ensure high chemical purity and isomeric integrity. Certificates of Analysis (COA) with detailed specifications are provided for every shipment, ensuring traceability and compliance with your research and development requirements.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry, and well-ventilated place at room temperature (15-25°C). This compound is hygroscopic (moisture-sensitive) and should be handled under an inert atmosphere (argon or nitrogen) for long-term storage and when dispensing to prevent degradation.

Specification

Item	Specification
Appearance	Colorless to pale yellow liquid
Identification (NMR)	Conforms to structure
Purity (HPLC/GC)	≥95% (Area %)
Isomeric Purity (E/Z ratio)	≥98:2 (E:Z)
Water Content (KF)	≤0.5%

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.