4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane
• CAS No.: 950761-81-6
• Molecular Formula: C26H23BO2
• Molecular Weight: 378.278
• Hs Code.: 2934999090
• Mol file: 950761-81-6.mol

Synonyms:4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(3-perylenyl)-1,3,2-dioxaborolane;(3-Perylenyl)boronic acid pinacol ester

Chemical Property of 4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 234.0 to 238.0 °C
• Boiling Point: 570.4±19.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 6.03640
• Solubility.: slightly sol. in Chloroform

Purity/Quality:

97% ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(3-perylenyl)-1,3,2-dioxaborolane >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,4,5,5-tetraMethyl-2-(perylen-3-yl)-1,3,2-dioxaborolane

There total 7 articles about 4,4,5,5-tetraMethyl-2-(perylen-3-yl)-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: 91.0%

3-bromoperylene (23683-68-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-((perylene-3-yl)phenyl)-1,3,2-dioxaborolan (950761-81-6)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 70 ℃; for 15h;

DOI:10.1021/jo702019p

Reference yield: 64.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Triisopropyl borate (5419-55-6) + 3-bromoperylene (23683-68-3) → 4,4,5,5-tetramethyl-2-((perylene-3-yl)phenyl)-1,3,2-dioxaborolan (950761-81-6)

Guidance literature:

3-bromoperylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; In tetrahydrofuran; hexane; at 20 ℃; for 69h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.202102052

Reference yield: 52.0%

PERYLENE (198-55-0) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-((perylene-3-yl)phenyl)-1,3,2-dioxaborolan (950761-81-6)

Guidance literature:

PERYLENE; bis(pinacol)diborane; With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; 1,2-bis-(dicyclohexylphosphino)ethane; In 5,5-dimethyl-1,3-cyclohexadiene; at 20 ℃; for 0.166667h; Schlenk technique; Inert atmosphere; Sealed tube;

With 2,2,2-trifluoroethanol; In 5,5-dimethyl-1,3-cyclohexadiene; at 80 ℃; for 36h; regioselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.9b02333

upstream raw materials:

3-bromoperylene

bis(pinacol)diborane

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

(perylene-3-yl)boronic acid

Downstream raw materials:

C₂₆H₁₁BrF₄

3-phenylperylene