7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Base Information

• Chemical Name: 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 642494-37-9
• Molecular Formula: C14H18BNO2
• Molecular Weight: 243.113
• Hs Code.: 2934999090
• European Community (EC) Number: 802-001-9
• DSSTox Substance ID: DTXSID30460557
• Nikkaji Number: J2.831.895B
• Wikidata: Q72482947
• Mol file: 642494-37-9.mol

Synonyms:642494-37-9;7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;Indole-7-boronic acid pinacol ester;INDOLE-7-BORONIC ACID, PINACOL ESTER;MFCD08669591;7-4,4,5,5-Tetramethyl)-1,3,2-dioxaborolan-2-yl)-1H-indole;1H-INDOLE, 7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1H-INDOL-7-YLBORONIC ACID PINACOL ESTER;(1H-INDOL-7-YL)BORONIC ACID PINACOL ESTER;SCHEMBL2028185;DTXSID30460557;QAXZRSICOHKXML-UHFFFAOYSA-N;AKOS000283802;CS-W022521;PB22194;DS-16983;SY027960;FT-0687417;EN300-212611;P10613;A834690;W-203387;Z2044785193;7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole

Chemical Property of 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Chemical Property:

• Vapor Pressure: 4.03E-06mmHg at 25°C
• Melting Point: 94-96 °C
• Refractive Index: 1.562
• Boiling Point: 396 °C at 760 mmHg
• PKA: 17.01±0.30(Predicted)
• Flash Point: 193.3 °C
• PSA: 34.25000
• Density: 1.11 g/cm³
• LogP: 2.46710
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 243.1430590
• Heavy Atom Count: 18
• Complexity: 316

Purity/Quality:

98%,99%, ^*data from raw suppliers

Indole-7-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C3C(=CC=C2)C=CN3
• Uses: Indole-7-boronic acid, pinacol ester

Technology Process of 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

There total 18 articles about 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 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: 88.0%

7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-trimethylsilanylindole (919119-70-3) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole (642494-37-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃; for 21h;

DOI:10.1021/ja0631652

Reference yield: 87.0%

→ 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole (642494-37-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 130 ℃; for 12h; Inert atmosphere;

Reference yield: 86.0%

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole (642494-37-9)

Guidance literature:

indole; With H₂SiEt₂; di-μ-chlorobis[(p-cymene)chlororuthenium](II); In toluene; at 90 ℃; for 13h;

bis(pinacol)diborane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; di-tert-butyl-2,2-bipyridine; In tetrahydrofuran; at 80 ℃; for 16h;

DOI:10.1002/ejoc.201700705

upstream raw materials:

7-bromo-1H-indole

bis(pinacol)diborane

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

7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-trimethylsilanylindole

Downstream raw materials:

3-cyclohexyl-1H,1'H-[2,7']biindolyl-6-carboxylic acid methyl ester

3-cyclohexyl-1-(2-methoxymethoxyethyl)-1H,1'H-[2,7']biindolyl-6-carboxylic acid methyl ester

7-(phenyl)-1H-indole

7-cinnamylindole

Refernces

• 1、 Zhao, Jia-Hui,Zhou, Zhao-Zhao,Zhang, Yue,Su, Xuan,Chen, Xi-Meng,Liang, Yong-Min. "Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex". supporting information. p. 4390 - 4394. Retrieved 2020/10/20.
• 2、 Iqbal, Saqib A.,Cid, Jessica,Procter, Richard J.,Uzelac, Marina,Yuan, Kang,Ingleson, Michael J.. "Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3". . p. 15381 - 15385. Retrieved 2019/10/22.