2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 709022-63-9
• Molecular Formula: C20H21BO2
• Molecular Weight: 304.197
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID30594886
• Nikkaji Number: J2.058.599D
• Wikidata: Q82489804
• Mol file: 709022-63-9.mol

Synonyms:709022-63-9;2-(anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;9-Anthraceneboronic acid piacol ester;9-Anthraceneboronic acid pinacol ester;2-anthracen-9-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD24039741;2-(9-Anthryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;SCHEMBL732170;YSCK0658;DTXSID30594886;9-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene;AKOS025392330;AS-2666;Anthracene-9-boronic Acid Pinacol Ester;SY234238;DB-192396;CS-0175540;T71257;EN300-7416658;A866525;7-Methoxy-8-(3-methyl-2-oxo-but-3-enyl)-chromen-2-one

Chemical Property of 2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 139.0 to 143.0 °C
• Boiling Point: 465.5±14.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 4.29220
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 304.1634601
• Heavy Atom Count: 23
• Complexity: 409

Purity/Quality:

97% ^*data from raw suppliers

9-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene ^*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=C3C=CC=CC3=CC4=CC=CC=C24
• Uses: 9-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene is a reactant in the synthesis of a series of luminescent compounds.

Technology Process of 2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about 2-(Anthracen-9-yl)-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: 64.0%

9-Bromoanthracene (1564-64-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 9,10-phenanthrenequinone (84-65-1) + 2-anthracen-9-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (709022-63-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In toluene; for 24h; Inert atmosphere; Reflux; Photolysis;

DOI:10.1016/j.tet.2013.12.045

Reference yield: 61.0%

9-Bromoanthracene (1564-64-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → anthracene (120-12-7) + 2-anthracen-9-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (709022-63-9)

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

Reference yield: 91.0%

2-methylphenyl bromide (95-46-5) + 2-anthracen-9-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (709022-63-9) → 9-(2-methylphenyl)anthracene (23674-13-7)

Guidance literature:

With Aliquat 336; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; toluene; at 90 ℃; for 7h;

upstream raw materials:

9-Bromoanthracene

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

Downstream raw materials:

Zn(C₂₀H₈N₄(C₁₄H₉)2(C₆H₃(C(CH₃)3)2)2)

2,4-bis[3-(9-anthryl)phenyl]-6-phenyl-1,3,5-triazine

[5,15-bis(anthracen-9-yl)-10,20-diphenylporphyrinato]nickel(II)

[5-(anthracen-9-yl)-10,20-bis(3,5-di-tert-butylphenyl)-15-phenylporphyrinato]nickel(II)

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