269409-99-6

Basic information

• Product Name: 2-Ethoxycarbonylphenylboronic acid pinacol ester
• Synonyms: 2-ETHOXYCARBONYLPHENYLBORONIC ACID, PINACOL ESTER;ETHYL 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;Ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate,min.97%;2-carboethoxyphenylboronic acid pinacol ester;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(ethoxycarbonyl)benzene;2-(Ethoxycarbonyl)phenylboronic acid, pinacol cyclic ester;2-Carboethoxyphenylboronic acid pinacol ester, Ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;Ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, min. 97%
• CAS NO: 269409-99-6
• Molecular Formula: C₁₅H₂₁BO₄
• Molecular Weight: 276.14
• Product Categories: Heterocyclic Compounds;organic or inorganic borate
• Mol File: 269409-99-6.mol

Chemical Properties

• Melting Point: 60-65 °C
• Boiling Point: 378 °C at 760 mmHg
• Flash Point: 182.4 °C
• Appearance: white to yellow/Powder
• Density: 1.07 g/cm³
• Vapor Pressure: 6.47E-06mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Ethoxycarbonylphenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxycarbonylphenylboronic acid pinacol ester(269409-99-6)
• EPA Substance Registry System: 2-Ethoxycarbonylphenylboronic acid pinacol ester(269409-99-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 269409-99-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Ethoxycarbonylphenylboronic acid pinacol ester is used as a reagent in organic synthesis for its ability to participate in cross-coupling reactions, facilitating the formation of stable and selective bonds with a variety of organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Ethoxycarbonylphenylboronic acid pinacol ester is utilized as a key intermediate in the synthesis of biologically active compounds, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Development:
Similarly, in agrochemical research, this compound is employed as a building block for the creation of active ingredients in pesticides and other agricultural products, enhancing crop protection and yield.
Used in Material Science:
2-Ethoxycarbonylphenylboronic acid pinacol ester is also studied for its potential applications in material science, where its unique bonding properties could contribute to the development of new materials with specific properties.
Used in Catalysis:
Furthermore, this versatile compound has been investigated for use in catalysis, where it may play a role in enhancing the efficiency of chemical reactions, thus impacting various industrial processes.

InChI:InChI=1/C15H21BO4/c1-6-18-13(17)11-9-7-8-10-12(11)16-19-14(2,3)15(4,5)20-16/h7-10H,6H2,1-5H3

Upstream product

• 93-89-0 benzoic acid ethyl ester 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1829-28-3 ethyl 2-iodobenzoate 
• 73183-34-3 bis(pinacol)diborane 
• 65-85-0 benzoic acid 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 7335-25-3 ethyl 2-chlorobenzoate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 927802-39-9 2-(1,3-thiazol-2-yl)benzoic acid 
• 1332358-75-4 ethyl 2-(pyrimidin-2-yl)benzoate 

Relevant articles and documents

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

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A new air-stable Si,S-chelating ligand for Ir-catalyzed directed: Ortho C-H borylation

A new air-stable Si,S-chelating ligand has been developed and used in an iridium-catalyzed ortho C-H borylation reaction with a broad substrate scope. This study provides the first example of using a sulfur-containing ligand in the catalytic C-H borylation process. It provides a rapid, efficient, and economical method for the preparation of organoboron compounds. This journal is

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N,B-bidentate boryl ligand-supported iridium catalyst for efficient functional-group-directed C-H borylation

Convenient silylborane precursors for introducing N,B-bidentate boryl ligands onto transition metals were designed, prepared, and employed in ready formation of irdium(IIl) complexes via Si-B oxidative addition. A practical, efficient catalytic ortho-borylation reaction of arenes with a broad range of directing groups was developed using an in situ generated catalyst from the silylborane preligand 3c and [IrCl(COD)]2.

Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters

An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.

The method for producing the phenyl boronic acid ester

PROBLEM TO BE SOLVED: To provide a method for producing phenylboronic acid esters in good yield from diborons and aryl halides by using a nickel catalyst and a base. SOLUTION: In the method for producing phenylboronic acid esters represented by general formula (3), wherein A is an ethylene group or the like which may be substituted by a methyl group, R1is a fluorine atom or the like, and m is an integer of 0-5; diborons and a chlorobenzene derivative are reacted with each other by using a trimethylphosphine coordinated nickel catalyst and alkoxides. COPYRIGHT: (C)2013,JPOandINPIT

Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki-Miyaura coupling without intentionally added base

We found that an integrated flow microreactor system enables the preparation of boronic esters bearing electrophilic functional groups using organolithium chemistry and that it allows for their use in Suzuki-Miyaura cross-coupling without intentionally added base. Based on this method, cross-coupling of two aryl halides bearing electrophilic functional groups was accomplished to obtain the corresponding biaryl compounds in one flow.

NiCl2(PMe3)2-catalyzed borylation of aryl chlorides

The cross-coupling of aryl chlorides and bis(pinacolato)diboron was achieved using NiCl2(PMe3)2 catalyst in the presence of metal 2,2,2-trifluoroethoxide. The catalyst smoothly provided the desired products regardless of a variety of functional groups and substituted positions.

Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron catalyzed by iridium-phosphine complexes

Iridium complexes generated from [Ir(OMe)(COD)]2 and tris[3,5-bis(trifluoromethyl)phenyl]phosphine efficiently catalyzed the ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron in octane at 80 °C to produce the corresponding ary

A novel transmetallation of arylzinc species into arylboronates from aryl halides in a barbier procedure

A variety of functionalized arylboronates are obtained in moderate to excellent yield by a one-step chemical procedure from the corresponding halides and a haloboronic ester via an intermediate arylzinc species. The Royal Society of Chemistry.