850567-55-4 | 1-(4-FLUOROPHENYL)VINYLBORONIC ACID, PINACOL ESTER

CAS:850567-55-4 | 1-(4-FLUOROPHENYL)VINYLBORONIC ACID, PINACOL ESTER,Description

“2-(1-(4-Fluorophenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane” is a chemical compound. It is also known as 1-(4-Fluorophenyl)vinylboronic acid pinacol ester. Its molecular weight is 248.11.

Chemical Reactions Analysis

The compound is known to be a reactant for Suzuki-Miyaura coupling reactions. It’s also used in the preparation of biologically and pharmacologically active molecules and conjugate addition reactions.

Physical And Chemical Properties Analysis

The compound has a boiling point of 277.8°C at 760 mmHg and a melting point of 38-42°C. It is a solid at room temperature.

Scientific Research Applications

Selective Synthesis Applications

A study by Szudkowska‐Fratczak et al. (2014) discusses the highly selective synthesis of 1-substituted (E)-buta-1,3-dienes using a palladium-catalyzed Suzuki–Miyaura cross-coupling method, involving 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane. This compound serves as a versatile vinyl building block, demonstrating high chemoselectivity for the Suzuki–Miyaura pathway over the Heck coupling process (Szudkowska‐Fratczak et al., 2014) .

Catalytic Applications

Fritschi et al. (2008) report on the preparation of 4,4,5,5-Tetraphenyl-1,3,2-dioxaborolane and its effectiveness in catalyzing the hydroboration of alkenes under certain conditions, forming stable organoboronate esters. This highlights the compound's potential as a catalyst in organic synthesis and its applicability in creating diverse organoboronate esters (Fritschi et al., 2008).

Application in Synthesis of N-Allylic Hydroxylamines

Pandya et al. (2003) explored the use of vinylboronic esters of pinacol (including 4,4,5,5-tetramethyl-1,3,2-dioxaborolanes) in the activation with dimethylzinc for the nucleophilic addition to nitrones. This process results in the efficient production of N-allylic hydroxylamines, a significant advancement in the synthesis of this compound class (Pandya et al., 2003) .

Thermal Neutron Detection

Mahl et al. (2018) discuss the synthesis of a novel 10 B enriched molecule, incorporating 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane, for enhanced thermal neutron detection. This application in radiation detection technology signifies a novel use of the compound in the field of nuclear physics and materials science (Mahl et al., 2018).

Polymer Synthesis Applications

In a study by Das et al. (2015), novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)-1,3,2 dioxaborolane derivatives were synthesized. These derivatives were used to synthesize boron-containing resveratrol analogues and conjugated polyenes, potentially useful in LCD technology and as therapeutic agents for neurodegenerative diseases (Das et al., 2015).

Safety And Hazards

The compound is considered hazardous. It may cause skin irritation, serious eye irritation, and respiratory irritation. It’s recommended to handle it with protective gloves, eye protection, and face protection.

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