480424-68-8

Basic information

• Product Name: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL ACETATE
• Synonyms: 2-dioxaborolan-2-yl)phenylacetate;2-Acetoxybenzeneboronic acid, pinacol ester;2-[2-(tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate;2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL ACETATE;2-ACETOXYPHENYLBORONIC ACID, PINACOL ESTER;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenylacetate,min.97%;2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL ACETATE, MIN. 97%;2-Acetoxyphenylboronic acid pinacol ester,2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate
• CAS NO: 480424-68-8
• Molecular Formula: C₁₄H₁₉BO₄
• Molecular Weight: 262.11
• Product Categories: organic or inorganic borate;Heterocyclic Compounds
• Mol File: 480424-68-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 47-51 °C(lit.)
• Boiling Point: 358.9°Cat760mmHg
• Flash Point: >230 °F
• Appearance: colorless/crystal
• Density: 1.08g/cm³
• Vapor Pressure: 2.46E-05mmHg at 25°C
• Refractive Index: 1.498
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL ACETATE(480424-68-8)
• EPA Substance Registry System: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL ACETATE(480424-68-8)

Safety Data

• Hazard Codes: N
• Statements: 40-51/53
• Safety Statements: 61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 480424-68-8(Hazardous Substances Data)

Usage

General Description

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate is a chemical compound that is commonly used in organic synthesis as a reagent for the preparation of various pharmaceutical and agrochemical products. It is a boron-containing compound that exhibits high reactivity and excellent selectivity towards a wide range of functional groups. This chemical finds application in the formation of carbon-carbon and carbon-heteroatom bonds, as well as in the synthesis of complex organic molecules. Its unique structure and reactivity make it a valuable tool in the field of chemical synthesis and medicinal chemistry.

InChI:InChI=1/C14H19BO4/c1-10(16)17-12-9-7-6-8-11(12)15-18-13(2,3)14(4,5)19-15/h6-9H,1-5H3

Upstream product

• 108-95-2 phenol 
• 122-79-2 Phenyl acetate 
• 73183-34-3 bis(pinacol)diborane 
• 50-78-2 aspirin 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Relevant articles and documents

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

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

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.