Indole-7-boronic acid

Base Information

• Chemical Name: Indole-7-boronic acid
• CAS No.: 210889-31-9
• Molecular Formula: C8H8BNO2
• Molecular Weight: 160.968
• Hs Code.: 2933299090
• European Community (EC) Number: 872-920-8
• DSSTox Substance ID: DTXSID40376872
• Nikkaji Number: J979.449B
• Wikidata: Q72482927
• Mol file: 210889-31-9.mol

Synonyms:Indole-7-boronic acid;210889-31-9;(1H-Indol-7-yl)boronic acid;1H-indol-7-ylboronic Acid;1H-Indole-7-boronic acid;Indole-7-BoronicAcid;Boronic acid, 1H-indol-7-yl-;(1H-Indol-7-yl)boronicacid;7-indolylboronic acid;SCHEMBL1688592;(1H-Indole-7-yl)boronic acid;DTXSID40376872;HABOMNOJYJNVHE-UHFFFAOYSA-N;MFCD07787388;AKOS015854481;MB05097;BS-22064;A4573;CS-0175033;FT-0691087;C90428;EN300-212612

Chemical Property of Indole-7-boronic acid

Chemical Property:

• Vapor Pressure: 2.83E-08mmHg at 25°C
• Refractive Index: 1.662
• Boiling Point: 433.2 °C at 760 mmHg
• PKA: 9.20±0.30(Predicted)
• Flash Point: 215.8 °C
• PSA: 56.25000
• Density: 1.33 g/cm³
• LogP: -0.15230
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• 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% ^*data from raw suppliers

Indole-7-boronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C2C(=CC=C1)C=CN2)(O)O
• Uses: Indole-7-boronic Acid acts as a reagent in the preparation of pyridineamines with inhibitory and antitumor activities against small cell lung cancer.

Technology Process of Indole-7-boronic acid

There total 1 articles about Indole-7-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:

7-bromo-1H-indole (51417-51-7) + Trimethyl borate (121-43-7,63156-11-6) → indole (120-72-9) + (1H-indol-7-yl)boronic acid (210889-31-9)

Guidance literature:

7-bromo-1H-indole; With potassium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.333333h; Inert atmosphere;

With tert.-butyl lithium; In tetrahydrofuran; mineral oil; pentane; at -78 - 20 ℃; for 0.25h; Darkness; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; mineral oil; pentane; at 20 ℃; for 3h; Overall yield = 213 mg; Inert atmosphere;

DOI:10.1016/j.ejmech.2019.111917

Reference yield: 87.0%

2-bromoanisole (578-57-4) + (1H-indol-7-yl)boronic acid (210889-31-9) → 7-(2-methoxyphenyl)indole

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; toluene; for 5h; Heating;

DOI:10.1021/jo0491612

Reference yield: 68.0%

6-bromo-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one (1444006-14-7) + (1H-indol-7-yl)boronic acid (210889-31-9) → 6-(1H-indol-7-yl)-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one (1444006-27-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; for 15h; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2013.04.008

upstream raw materials:

7-bromo-1H-indole

Trimethyl borate

Downstream raw materials:

1-(1-benzylpiperidin-4-yl)-6-(1H-indol-7-yl)-4-morpholin-4-yl-1H-pyrazolo[3,4-d]pyrimidine

(+/-)-4-benzyl-5-chloro-1,4-dihydro-6-(indol-7-yl)-2,2,4,8-tetramethyl-2H-quinolin-3-one

6-(1H-indol-7-yl)-1-(3,4,5-trimethoxyphenyl)pyridin-2(1H)-one

(S)-2-(1-((5-(1H-indol-7-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Refernces