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

Base Information

• Chemical Name: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 476004-81-6
• Molecular Formula: C14H18 B N O2
• Molecular Weight: 243.113
• Hs Code.: 2934999090
• European Community (EC) Number: 898-982-6
• DSSTox Substance ID: DTXSID60463430
• Nikkaji Number: J1.741.485B
• Wikidata: Q72499859
• Mol file: 476004-81-6.mol

Synonyms:476004-81-6;2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;INDOLE-2-BORONIC ACID PINACOL ESTER;2-(PINACOLATEBORYL)INDOLE;1H-Indole-2-boronic acid pinacol ester;(1H-INDOL-2-YL)BORONIC ACID PINACOL ESTER;MFCD09751284;2-Pinacolateboryl Indole;SCHEMBL824089;YSCK0382;DTXSID60463430;IAQBURSQTCOSBP-UHFFFAOYSA-N;AKOS016001837;MB07604;1h-indol-2-ylboronic acid pinacol ester;AS-42748;SY256480;Indole-2-boronic acid pinacol ester, 95%;CS-0091620;FT-0754971;EN300-209009;J-505876;Z3235023463;2-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE;1H-Indole, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

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

Chemical Property:

• Melting Point: 84-85 ºC
• Boiling Point: 396 ºC
• PKA: 16.76±0.30(Predicted)
• Flash Point: 193 ºC
• PSA: 34.25000
• Density: 1.11
• LogP: 2.46710
• Storage Temp.: Refrigerated.
• 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:

97% ^*data from raw suppliers

Indole-2-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=CC3=CC=CC=C3N2

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

There total 2 articles about 2-(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:

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole (919119-72-5) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (476004-81-6)

Guidance literature:

With catalyst: (Ir(C₈H₁₂)Cl)2/(NC₅H₄C(CH₃)3-4)2; In tetrahydrofuran; react. indole and benzene with boron compds. in THF in the presence of Ir complex and 4,4'-di-tert-butylbipyridine at 80°C; workup with 3 M aq. sodium acetate;

DOI:10.1021/ja1006405

Reference yield:

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole (919119-72-5) + 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (476004-81-6)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/ja1006405

Reference yield: 92.0%

trifluoromethanesulfonic acid 3-phenyl-isoxazol-5-yl ester (454253-30-6) + 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (476004-81-6) → 5-(1H-indol-2-yl)-3-phenylisoxazole

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; at 100 ℃;

DOI:10.1002/ejoc.201900187

upstream raw materials:

indole

bis(pinacol)diborane

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

benzene

Downstream raw materials:

2-(2-thienyl)indole

2-(2-Fluorophenyl)-1H-indole

2-(4-methylphenyl)-1H-indole

2-o-tolyl-1H-indole