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

Base Information

• Chemical Name: 2-(3-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 594823-67-3
• Molecular Formula: C12H16BBrO2
• Molecular Weight: 282.973
• Hs Code.: 2934999090
• European Community (EC) Number: 805-466-6
• DSSTox Substance ID: DTXSID80433892
• Nikkaji Number: J2.509.157D
• Wikidata: Q82248163
• Mol file: 594823-67-3.mol

Synonyms:594823-67-3;2-(3-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-Bromophenylboronic acid pinacol ester;3-Bromophenylboronic acid, pinacol ester;1,3,2-Dioxaborolane, 2-(3-bromophenyl)-4,4,5,5-tetramethyl-;3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene;MFCD12545926;(3-BROMOPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL5892478;AMY8912;DTXSID80433892;FHCWGLQDAMYXJS-UHFFFAOYSA-N;AKOS016001641;AS-2621;CS-W000950;SY056852;B6024;FT-0686849;EN300-1425718;A869197;Z2044819436;2-(3-Bromophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-(m-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Chemical Property:

• Melting Point: 48 °C
• Boiling Point: 333.2±25.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 2.74830
• Storage Temp.: Room temperature.
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 282.04267
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

97% ^*data from raw suppliers

3-BroMophenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 26 articles about 2-(3-Bromophenyl)-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: 99.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (3-bromophenyl)boronic acid (89598-96-9) → (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene) (594823-67-3)

Guidance literature:

With calcium sulfate; In toluene; for 3.5h; Heating;

DOI:10.1021/jo0710329

Reference yield: 80.0%

m-Bromoaniline (591-19-5) + bis(pinacol)diborane (73183-34-3) → (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene) (594823-67-3)

Guidance literature:

m-Bromoaniline; With fluoroboric acid; sodium nitrite; In water; at 0 ℃; for 1h; Inert atmosphere; Schlenk technique;

bis(pinacol)diborane; With methanol; at 22 - 25 ℃; for 36h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.3184/174751918X15362432558247

Reference yield: 79.0%

1,3-dibromobenzene (108-36-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → bromobenzene (108-86-1,52753-63-6) + (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene) (594823-67-3)

Guidance literature:

With copper(l) iodide; iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine; sodium hydride; In tetrahydrofuran; mineral oil; at -10 ℃; Inert atmosphere;

DOI:10.1021/ol500675q

upstream raw materials:

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

(3-bromophenyl)boronic acid

1,3-dibromobenzene

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

Downstream raw materials:

phenyl-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

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

4-bromo-(2-(3-bromophenyl))pyridine

2-(3-bromophenyl)pyridine