1377024-34-4

Basic information

• Product Name: (E)-ethyl 3-(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate
• Synonyms: (E)-ethyl 3-(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate
• CAS NO: 1377024-34-4
• Molecular Formula: C17H23BO4
• Molecular Weight: 302.17312
• Mol File: 1377024-34-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 421.9±28.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (E)-ethyl 3-(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-ethyl 3-(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate(1377024-34-4)
• EPA Substance Registry System: (E)-ethyl 3-(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate(1377024-34-4)

Safety Data

• Hazardous Substances Data: 1377024-34-4(Hazardous Substances Data)

Usage

General Description

"(E)-ethyl 3-(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate" is a chemical compound that belongs to the class of acrylate compounds. It contains a boron-containing heterocycle, specifically a 1,3,2-dioxaborolane ring. The compound is an important reagent in organic synthesis, often used in palladium-catalyzed cross-coupling reactions to form carbon-carbon bonds. It is also used in the production of polymer materials and pharmaceutical intermediates. Additionally, its unique structure and reactivity make it a valuable tool in chemical research and development.

Upstream product

• 480425-35-2 methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 140-88-5 ethyl acrylate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 98-80-6 phenylboronic acid 
• 380151-86-0 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarboxaldehyde 

Relevant articles and documents

Meta -Selective C-H functionalisation of aryl boronic acids directed by a MIDA-derived boronate ester

N-Methyliminodiacetic acid (MIDA) boronates are boronic acid derivatives which are stable to reduction, oxidation and transmetalation. This has led to their widespread use as boronic acid protecting groups (PGs) and in iterative cross-couplings. We describe herein the development of a novel MIDA derivative that acts in a dual manner, as a protecting group and a directing group (DG) for meta C(sp2)-H functionalisation of arylboronic acids. Palladium catalysed C-H alkenylations, acetoxylations and arylations are possible, at room temperature and under aerobic conditions. Deprotection to reveal the functionalised boronic acids is rapid and allows for full recovery of the DG. The technique allows the facile diversification of aryl boronic acids and their subsequent use in a range of reactions or in iterative processes.

Lewis Base Activation of Silyl Acetals: Iridium-Catalyzed Reductive Horner-Wadsworth-Emmons Olefination

A Lewis base promoted deprotonative pronucleophile addition to silyl acetals has been developed and applied to the iridium-catalyzed reductive Horner-Wadsworth-Emmons (HWE) olefination of esters and the chemoselective reduction of the resulting enoates. Lewis base activation of silyl acetals generates putative pentacoordinate silicate acetals, which fragment into aldehydes, silanes, and alkoxides in situ. Subsequent deprotonative metalation of phosphonate esters followed by HWE with aldehydes furnishes enoates. This operationally convenient, mechanistically unique protocol converts the traditionally challenging aryl, alkenyl, and alkynyl esters to homologated enoates at room temperature within a single vessel.