Indole-6-boronic acid

Base Information

• Chemical Name: Indole-6-boronic acid
• CAS No.: 147621-18-9
• Molecular Formula: C8H8BNO2
• Molecular Weight: 160.968
• Hs Code.: 2933990090
• European Community (EC) Number: 627-185-6
• DSSTox Substance ID: DTXSID10376809
• Nikkaji Number: J979.448D
• Wikidata: Q72482930
• ChEMBL ID: CHEMBL4071778
• Mol file: 147621-18-9.mol

Synonyms:Indole-6-boronic acid;147621-18-9;1H-indol-6-ylboronic Acid;6-Indolylboronic Acid;(1H-indol-6-yl)boronic acid;6-Indoleboronic acid;Indole-6-BoronicAcid;6-BORONOINDOLE;1H-INDOL-6-YL-6-BORONIC ACID;1H-INDOLE-6-BORONIC ACID;Boronic acid, 1H-indol-6-yl-;6-indole boronic acid;1~{H}-indol-6-ylboronic acid;CHEMBL4071778;MFCD03095176;Boronic acid,B-1H-indol-6-yl-;indol-6-boronic acid;SCHEMBL6091;1H-indol-6-yl-boronic acid;1H-indole-6-yl-boronic acid;(1H-Indole-6-yl)boronic acid;DTXSID10376809;ZVMHOIWRCCZGPZ-UHFFFAOYSA-N;BCP27170;STR09340;INDOLE-6-BORONIC ACID 98%;BDBM50266944;AKOS005259574;AM86614;PB15735;6-Indolylboronic acid;Indole-6-boronic Acid;CS-0007655;FT-0651525;I0803;EN300-212520;J-500195;JB8

Chemical Property of Indole-6-boronic acid

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 177-181 °C
• Refractive Index: 1.662
• Boiling Point: 433.229 °C at 760 mmHg
• PKA: 9.00±0.30(Predicted)
• Flash Point: 215.81 °C
• PSA: 56.25000
• Density: 1.331 g/cm³
• LogP: -0.15230
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 161.0648087
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

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

Indole-6-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)C=CN2)(O)O
• Uses: Reactant involved in synthesis of:Indole compounds for use as HIV-1 glycoprotein-41 fusion inhibitorsδ-Carbolines / carbozolesTrisubstituted pyrimidines as PI3K inhibitors(Thienopyridine)carboxamides as CHK1 inhibitorscis-FluorostilbenesReactant involved in Suzuki-Miyaura reactions

Technology Process of Indole-6-boronic acid

There total 11 articles about Indole-6-boronic acid 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: 80.0%

potassium (1H-indol-6-yl)trifluoroborate → 6-indolylboronic acid (147621-18-9)

Guidance literature:

With water; silica gel; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo901441u

Reference yield: 68.0%

6-bromo-1H-indole (52415-29-9) + boric acid tributyl ester (688-74-4) + tert.-butyl lithium (594-19-4) → 6-indolylboronic acid (147621-18-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; dichloromethane; pentane;

Reference yield:

6-bromo-1H-indole (52415-29-9) → 6-indolylboronic acid (147621-18-9)

Guidance literature:

6-bromo-1H-indole; With potassium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h;

With tert.-butyl lithium; In tetrahydrofuran; pentane; for 0.166667h;

With Trimethyl borate; In tetrahydrofuran; pentane; at -78 - 20 ℃;

DOI:10.1021/jo0491612

upstream raw materials:

6-bromo-1H-indole

4-bromo-2-nitrotoluene

boric acid tributyl ester

tert.-butyl lithium

Downstream raw materials:

6-(pyridin-3-yl)-1H-indole

C₁₄H₁₅NO

6-[2-(2-phenylbenzofuran-3-yl)benzo[b]thiophen-3-yl]-1H-indole

1-(cyclohexylmethyl)-6-(1H-indol-6-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

Refernces

• 1、 -. "Novel small molecule compounds, preparation method thereof and method for treating/preventing HIV-1 infected aids by using compound". . . Retrieved 2017/09/26.
• 2、 Molander, Gary A.,Cavalcanti, Livia N.,Canturk, Belgin,Pan, Po-Shen,Kennedy, Lauren E.. "Efficient hydrolysis of organotrifluoroborates via silica gel and water". supporting information; experimental part. p. 7364 - 7369. Retrieved 2010/01/16.