269410-00-6

Basic information

• Product Name: ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE
• Synonyms: ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ETHYL BENZOATE;3-ETHOXYCARBONYLPHENYLBORONIC ACID, PINACOL ESTER;Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate,min.97%;3-carboethoxyphenylboronic acid pinacol ester;3-Carboethoxyphenylboronic acid pinacol ester, Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, min. 97%;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS NO: 269410-00-6
• Molecular Formula: C₁₅H₂₁BO₄
• Molecular Weight: 276.14
• Product Categories: Heterocyclic Compounds;organic or inorganic borate;Aryl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 269410-00-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 40-44 °C(lit.)
• Boiling Point: 378.6 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: white/Powder
• Density: 1.07 g/cm³
• Vapor Pressure: 6.21E-06mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE(269410-00-6)
• EPA Substance Registry System: ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE(269410-00-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 269410-00-6(Hazardous Substances Data)

Usage

General Description

ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE is a chemical compound that belongs to the class of esters. It is derived from the reaction of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid with ethanol. ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE is often used as a building block in organic synthesis and chemical research. It has a variety of applications in the production of pharmaceuticals, agrochemicals, and functional materials.ETHYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE is considered to be a potentially hazardous substance and should be handled and stored with care.

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

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 24398-88-7 ethyl 3-bromobenzoate 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 
• 582-33-2 3-aminobenzoic acid ethyl ester 
• 73183-34-3 bis(pinacol)diborane 
• 1128-76-3 3-chloro-benzoic acid ethyl ester 
• 93-89-0 benzoic acid ethyl ester 
• 585-76-2 m-bromobenzoic acid 
• 1126479-87-5 C₁₆H₂₀BNO₄ 
• 58313-23-8 3-iodobenzoic acid methyl ester 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1442-02-0 ethyl 3-methylthiobenzoate 

Downstream Products

• 894416-25-2 2-(3,4,5-trimethoxyphenylamino)-6-(ethyl-3-benzoate)pyrazine 
• 1333419-36-5 (Z)-ethyl 3-(3-methoxy-3-oxo-1-(2-oxopyrrolidin-1-yl)prop-1-en-1-yl)benzoate 
• 451-02-5 ethyl 3-fluorobenzoate 
• 908334-19-0 3-(1-tert-butoxycarbonyl-3-piperidyl)benzoic acid 
• 33745-48-1 3-Ethenylbenzoic acid ethyl ester 

Relevant articles and documents

Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions

The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.

Copper-Photocatalyzed Borylation of Organic Halides under Batch and Continuous-Flow Conditions

The copper-photocatalyzed borylation of aryl, heteroaryl, vinyl and alkyl halides (I and Br) was reported. The reaction proceeded using a new heteroleptic Cu complex under irradiation with blue LEDs, giving the corresponding boronic-acid esters in good to excellent yields. The reaction was extended to continuous-flow conditions to allow an easy scale-up. The mechanism of the reaction was studied and a mechanism based on a reductive quenching (CuI/CuI*/Cu0) was suggested.

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.