2-(4-Bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Base Information

• Chemical Name: 2-(4-Bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane
• CAS No.: 183677-71-6
• Molecular Formula: C11H14 B Br O2
• Molecular Weight: 268.946
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID10439342
• Nikkaji Number: J1.843.555A
• Wikidata: Q82255266
• Mol file: 183677-71-6.mol

Synonyms:183677-71-6;2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane;4-Bromobenzeneboronic acid neopentyl glycol ester;4-Bromophenylboronic acid neopentyl glycol ester;4-Bromobenzeneboronic acid neopentyl glycol cyclic ester;SCHEMBL5528199;DTXSID10439342;MFCD01318105;AKOS004115091;AS-3040;CS-0174723;FT-0617858;E85419;A853405;2-(4-Bromophenyl)-5,5-dimethyl-2-bora-1,3-dioxane

Chemical Property of 2-(4-Bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 109-111°C
• Refractive Index: 1.533
• Boiling Point: 331°Cat760mmHg
• Flash Point: 154°C
• PSA: 18.46000
• Density: 1.33g/cm³
• LogP: 2.21730
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 268.02702
• Heavy Atom Count: 15
• Complexity: 205

Purity/Quality:

98%Min ^*data from raw suppliers

4-Bromophenylboronicacidneopentylglycolester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OCC(CO1)(C)C)C2=CC=C(C=C2)Br

Technology Process of 2-(4-Bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

There total 5 articles about 2-(4-Bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 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: 100.0%

4-Bromophenylboronic acid (5467-74-3) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane (183677-71-6)

Guidance literature:

In toluene; for 1h; Heating;

DOI:10.1016/j.tetlet.2006.02.012

Reference yield: 78.0%

1'-naphthacetophenone (941-98-0) + 4-Bromophenylboronic acid (5467-74-3) → 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane (183677-71-6)

Guidance literature:

With tris(triphenylphosphine)ruthenium(II) chloride; caesium carbonate; at 150 ℃; for 3h; Inert atmosphere;

Reference yield: 60.0%

tris(4-bromophenyl)antimony diacetate + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane (183677-71-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; at 60 ℃; for 12h;

DOI:10.1016/j.jorganchem.2014.04.006

upstream raw materials:

4-Bromophenylboronic acid

2,2-Dimethyl-1,3-propanediol

1.4-dibromobenzene

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

Downstream raw materials:

2,2-dimethylpropane-1,3-diyl [4-(trimethylsilylethynyl)phenyl] boronate

4-bromo-N,N-bis(propan-2-yl)aniline

4-bromo-N-cyclohexyl-N-(4-(4-nitrophenyl)butan-2-yl)aniline

5,5-dimethyl-2-[4-(oxetan-3-yloxy)phenyl]-1,3,2-dioxaborinane

Refernces

• 1、 Aryal, Vivek,Dhungana, Roshan K.,Giri, Ramesh,Lakomy, Margaret G.,Niroula, Doleshwar,Sapkota, Rishi R.. "Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination". supporting information. p. 19092 - 19096. Retrieved 2021/08/09.
• 2、 Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.. "Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters". supporting information. p. 482 - 487. Retrieved 2019/01/04.