2-(2-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 857934-82-8
• Molecular Formula: C12H16 B I O2
• Molecular Weight: 329.973
• Hs Code.: 2934999090
• European Community (EC) Number: 678-572-1
• DSSTox Substance ID: DTXSID90478835
• Nikkaji Number: J2.190.598D
• Wikidata: Q82312472
• Mol file: 857934-82-8.mol

Synonyms:2-(2-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;857934-82-8;1-Iodo-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;I0653;LCZC2542;DTXSID90478835;MFCD09038529;ZB1305;AKOS015853869;2-Iodophenylboronic Acid Pinacol Ester;CS-0173868;T73001;A841450;2-(2-iodanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(2-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.557
• Boiling Point: 348.407°C at 760 mmHg
• Flash Point: 164.511°C
• PSA: 18.46000
• Density: 1.468g/cm³
• LogP: 2.59040
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 330.02881
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Iodo-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2I

Technology Process of 2-(2-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 9 articles about 2-(2-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + ortho-iodophenylboronic acid (1008106-86-2) → 2-(2-iodophenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane (857934-82-8)

Guidance literature:

In toluene; for 2h; Reflux; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201915409

Reference yield: 86.0%

1,2-Diiodobenzene (615-42-9) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) → 2-(2-iodophenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane (857934-82-8)

Guidance literature:

1,2-Diiodobenzene; With TurboGrignard; In tetrahydrofuran; at -78 ℃; for 3h;

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/anie.200462928

Reference yield: 78.0%

1-Bromo-2-iodobenzene (583-55-1) + bis(pinacol)diborane (73183-34-3) → 2-(2-iodophenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane (857934-82-8)

Guidance literature:

bis(pinacol)diborane; With dimethyl zinc(II); magnesium 2-methylpropan-2-olate; In 1,4-dioxane; hexane; at 0 - 20 ℃; for 0.5h; Schlenk technique; Glovebox; Inert atmosphere;

1-Bromo-2-iodobenzene; In 1,4-dioxane; hexane; at 20 - 120 ℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere;

With iodine; In 1,4-dioxane; hexane; at 20 ℃; for 3h; Schlenk technique; Glovebox; Inert atmosphere;

DOI:10.1021/ja409748m

upstream raw materials:

1,2-Diiodobenzene

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2,3-dimethyl-2,3-butane diol

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

4,4,5,5-tetramethyl-2-[2-(2-propenyl)phenyl]-1,3,2-dioxaborolane

Refernces

• 1、 Nagashima, Yuki,Takita, Ryo,Yoshida, Kengo,Hirano, Keiichi,Uchiyama, Masanobu. "Design, generation, and synthetic application of borylzincate: Borylation of aryl halides and borylzincation of benzynes/terminal alkyne". supporting information. p. 18730 - 18733. Retrieved 2014/01/06.
• 2、 Baron, Oliver,Knochel, Paul. "Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents". . p. 3133 - 3135. Retrieved 2007/10/03.