857934-82-8

Basic information

• Product Name: 2-(2-IODOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• Synonyms: 2-Iodophenylboronic Acid Pinacol Ester;1-Iodo-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene 2-Iodophenylboronic Acid Pinacol Ester
• CAS NO: 857934-82-8
• Molecular Formula: C₁₂H₁₆BIO₂
• Molecular Weight: 329.97
• Product Categories: B (Classes of Boron Compounds);Boronic Acids Esters
• Mol File: 857934-82-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 348.407°C at 760 mmHg
• Flash Point: 164.511°C
• Appearance: /
• Density: 1.468g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: 2-(2-IODOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-IODOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(857934-82-8)
• EPA Substance Registry System: 2-(2-IODOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(857934-82-8)

Safety Data

• Hazardous Substances Data: 857934-82-8(Hazardous Substances Data)

Usage

Description

2-(2-IODOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is a boron-containing chemical compound with the molecular formula C12H17BO2I. It is a versatile building block used in organic synthesis for the preparation of various organic molecules.
Used in Pharmaceutical Industry:
2-(2-IODOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is used as a boronic acid derivative for the formation of carbon-carbon bonds in Suzuki-Miyaura coupling reactions. Its high stability and tolerance towards various reaction conditions make it an important tool in the field of organic chemistry, facilitating the development of new pharmaceutical compounds.
Used in Chemical Research:
2-(2-IODOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is used as a key intermediate in the synthesis of complex organic molecules for research purposes. Its unique properties allow for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various fields.

InChI:InChI=1/C12H16BIO2/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8H,1-4H3

Upstream product

• 615-42-9 1,2-Diiodobenzene 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1008106-86-2 ortho-iodophenylboronic acid 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 98-80-6 phenylboronic acid 
• 1692-26-8 bis(propan-2-yl) phenylboronate 
• 6063-74-7 1-methyl-2-phenyl-[1,3,2]diazaborinane 
• 583-55-1 1-Bromo-2-iodobenzene 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 857934-92-0 4,4,5,5-tetramethyl-2-[2-(2-propenyl)phenyl]-1,3,2-dioxaborolane 

Relevant articles and documents

Visible-Light-Driven Strain-Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters

There are a limited number of ring-contraction methodologies which convert readily available five-membered rings into strained four-membered rings. Here we report a photo-induced radical-mediated ring contraction of five-membered-ring alkenyl boronate complexes into cyclobutanes. The process involves the addition of an electrophilic radical to the electron-rich alkenyl boronate complex, leading to an α-boryl radical. Upon one-electron oxidation, ring-contractive 1,2-metalate rearrangement occurs to give a cyclobutyl boronic ester. A range of radical precursors and vinyl boronates can be employed, and chiral cyclobutanes can be accessed with high levels of stereocontrol. The process was extended to the preparation of benzofused cyclobutenes and the versatility of the boronic ester was demonstrated by conversion to other functional groups.

Ortho-magnesiation of boron-substituted benzenes by using (TMP) 2Mg

Magnesiation ortho to boron: Borylbenzenes with an N-methyl-1,3- ethylenediamino group on the boron atom undergo ortho-magnesiation upon exposure to 2,2,6,6-tetramethylpiperidide (TMP)2Mg, and the resulting ortho-magnesiated borylbenzenes can be trapped with electrophiles (see scheme).

Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents

(Chemical Equation Presented) It's all in the mix: The magnesiation of iodoaryl and iodoheteroaryl boronic esters with iPrMgCl·LiCl leads to mixed bimetallic compounds, which react with a variety of electrophiles to provide highly functionalized boronic e