4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane
• CAS No.: 68716-52-9
• Molecular Formula: C16H19BO2
• Molecular Weight: 254.137
• Hs Code.: 2934999090
• European Community (EC) Number: 675-017-5
• DSSTox Substance ID: DTXSID90375052
• Nikkaji Number: J902.924I
• Wikidata: Q82163595
• Mol file: 68716-52-9.mol

Synonyms:68716-52-9;4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane;Naphthalene-1-boronic acid pinacol ester;2-(1-Naphthylene)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1-NAPHTHYLBORONIC ACID PINACOL ESTER;naphthalene-1-boronic acid, pinacol ester;1-NAPHTHALENBORONIC ACID, PINACOL ESTER;4,4,5,5-tetramethyl-2-naphthalen-1-yl-1,3,2-dioxaborolane;MFCD05663869;4,4,5,5-TETRAMETHYL-2-(1-NAPHTHYL)-1,3,2-DIOXABOROLANE;SCHEMBL476862;DTXSID90375052;WQGRAXGAXSNSDL-UHFFFAOYSA-N;AKOS015960102;AB21985;AS-2647;SY034128;CS-0153835;FT-0641204;T3218;EN300-1425745;A836226;1-Naphthylboronic acid 2,3-dimethyl-2,3-butanediyl;J-513982;Naphthalene-1-boronic acid pinacol ester, AldrichCPR;2-(1-Naphthylene)-4,4,5,5-tetramethyl-1,3,2dioxaborolane;4,4,5,5-tetramethyl-2-(1-naphthalenyl)-1,3,2-dioxaborolane;1-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)NAPHTHALENE

Chemical Property of 4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 1.35E-05mmHg at 25°C
• Melting Point: 56-58 °C
• Refractive Index: 1.558
• Boiling Point: 378.7 °C at 760 mmHg
• Flash Point: 182.8 °C
• PSA: 18.46000
• Density: 1.06g/cm³
• LogP: 3.13900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate,
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 254.1478100
• Heavy Atom Count: 19
• Complexity: 324

Purity/Quality:

99% ^*data from raw suppliers

Naphthalene-1-boronic 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=CC3=CC=CC=C23
• Uses: Naphthalene-1-boronic Acid Pinacol Ester is a catalyst that is used in the synthesis of Tribenzo[de,h,kl]naphtho[1,2,3,4-rst]pentaphene (T767600), which is used in nanotechnology in the optical sensing of current dynamics in LED devices.

Technology Process of 4,4,5,5-Tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane

There total 13 articles about 4,4,5,5-Tetramethyl-2-(naphthalen-1-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: 85.0%

1-Iodonaphthalene (90-14-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → naphthalene (91-20-3,71998-51-1,72931-45-4) + 1-naphthylboronic acid pinacol ester (68716-52-9)

Guidance literature:

With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃; for 2h;

DOI:10.1021/jo991337q

Reference yield: 79.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-Iodonaphthalene (90-14-2) → naphthalene (91-20-3,71998-51-1,72931-45-4) + 1-naphthylboronic acid pinacol ester (68716-52-9)

Guidance literature:

1-Iodonaphthalene; With triethylamine; benzo[1,3,2]dioxaborole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃; for 12h;

2,3-dimethyl-2,3-butane diol; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/jo991337q

Reference yield: 76.0%

1-Bromonaphthalene (90-11-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → naphthalene (91-20-3,71998-51-1,72931-45-4) + 1-naphthylboronic acid pinacol ester (68716-52-9)

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

upstream raw materials:

1-Iodonaphthalene

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

1-Bromonaphthalene

1-naphthyl triflate

Downstream raw materials:

1-phenylnaphthalene

1,4-di(naphthalene-1-yl)benzene

1-(4-methylphenyl)naphthalene

α-naphthol

Refernces

• 1、 Geng, Shasha,Zhang, Juan,Chen, Shuo,Liu, Zhengli,Zeng, Xiaoqin,He, Yun,Feng, Zhang. "Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation". . p. 5582 - 5588. Retrieved 2020/07/08.
• 2、 Pinet, Sandra,Liautard, Virginie,Debiais, Mégane,Pucheault, Mathieu. "Radical Metal-Free Borylation of Aryl Iodides". . p. 4759 - 4768. Retrieved 2017/10/03.