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

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 937366-54-6
• Molecular Formula: C14H18BNO2
• Molecular Weight: 243.113
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60694404
• Nikkaji Number: J1.768.872C
• Wikidata: Q72482951
• Mol file: 937366-54-6.mol

Synonyms:937366-54-6;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;Indole-3-boronic acid pinacol ester;3-Indoleboronic Acid Pinacol Ester;MFCD09879158;SCHEMBL2111365;DTXSID60694404;WQPRSRMWYVTUTE-UHFFFAOYSA-N;AKOS015950042;MB08127;AS-41870;SY029280;PINACOL ESTER INDOLE-5-BORONIC ACID;CS-0137703;FT-0741444;A849899;2-(1H-Indole-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole

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

Chemical Property:

• Boiling Point: 396.0±15.0 °C(Predicted)
• PKA: 17.01±0.30(Predicted)
• PSA: 34.25000
• Density: 1.11
• LogP: 2.46710
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• 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:

99% ^*data from raw suppliers

Indole-3-boronicAcidPinacolEster ^*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=CNC3=CC=CC=C23

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

There total 13 articles about 3-(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: 78.0%

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Guidance literature:

With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel⁽⁰⁾; In hexane; at 60 ℃; for 4h; Solvent; Temperature; regioselective reaction; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1021/jacs.0c05434

Reference yield: 70.0%

3-bromoindole (1484-27-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Guidance literature:

3-bromoindole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at 20 ℃; for 5h;

Reference yield: 64.0%

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (942070-45-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Guidance literature:

at 180 ℃; for 0.75h;

DOI:10.1021/jo901822b

upstream raw materials:

3?(4,4,5,5?tetramethyl?1,3,2?dioxaborolan?2?yl)?1?(triisopropylsilyl)?1H?indole

1-(triisopropylsilyl)-1H-indole

bis(pinacol)diborane

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Downstream raw materials:

3-(2-nitrophenyl)-1H-indole

3-(2,5-dichloropyrimidine-4-yl)-1H-indole

Refernces

• 1、 -. "CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME". . . Retrieved 2020/02/29.
• 2、 Preshlock, Sean M.,Plattner, Donald L.,Maligres, Peter E.,Krska, Shane W.,Maleczka Jr., Robert E.,Smith III, Milton R.. "A traceless directing group for C - H borylation". . p. 12915 - 12919. Retrieved 2014/01/06.