Indole-4-boronic acid

Base Information

• Chemical Name: Indole-4-boronic acid
• CAS No.: 220465-43-0
• Molecular Formula: C8H8BNO2
• Molecular Weight: 160.968
• Hs Code.: 29339900
• European Community (EC) Number: 640-120-6
• DSSTox Substance ID: DTXSID90376786
• Nikkaji Number: J1.071.863E
• Wikidata: Q72482933
• Mol file: 220465-43-0.mol

Synonyms:Indole-4-boronic acid;220465-43-0;1H-indol-4-ylboronic Acid;(1H-indol-4-yl)boronic acid;4-Boronoindole;1h-indole-4-boronic acid;1H-INDOL-4-YL-4-BORONIC ACID;Boronic acid, 1H-indol-4-yl-;(1h)-indol-4-ylboronic acid;4-Indoleboronic acid;4-indolylboronic acid;4-indole boronic acid;4-indole-boronic acid;indole 4-boronic acid;1H-Indole-4-ylboronic acid;SCHEMBL19337;(1H-indol-4-yl)boronicacid;1H-indole-4-yl-boronic acid;DTXSID90376786;USJUQEVUEBCLLR-UHFFFAOYSA-N;indole-4-boronic acid, AldrichCPR;MFCD03095175;AKOS002670087;CS-W014327;PB14320;PS-9448;SB10372;A4740;AM20030369;FT-0607902;EN300-6480643;Q-102077;1H-indol-4-ylboronic acid;(1H-Indol-4-yl)boronic acid

Chemical Property of Indole-4-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: 9.00±0.30(Predicted)
• Flash Point: 215.8 °C
• PSA: 56.25000
• Density: 1.33 g/cm³
• LogP: -0.15230
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• 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-4-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C2C=CNC2=CC=C1)(O)O
• Uses: An arylboronic acid-based fluorescent biosensor.

Technology Process of Indole-4-boronic acid

There total 5 articles about Indole-4-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: 89.0%

4-bromo-1H-indole (52488-36-5) → indole-4-boronic acid (220465-43-0)

Guidance literature:

4-bromo-1H-indole; With tert.-butyl lithium; potassium hydride; In diethyl ether; at 0 ℃; for 0.833333h;

With boric acid tributyl ester; In diethyl ether; at 0 - 20 ℃;

With phosphoric acid; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/jo981778u

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) → indole-4-boronic acid (220465-43-0)

Guidance literature:

4-bromo-1H-indole; With sodium hydride; In diethyl ether; at 0 ℃; for 0.5h;

With n-butyllithium; In diethyl ether; hexane; for 0.5h; Cooling with acetone-dry ice;

Trimethyl borate; With phosphoric acid; water; more than 3 stages;

Reference yield:

4-bromo-1H-indole (52488-36-5) + boric acid tributyl ester (688-74-4) → indole-4-boronic acid (220465-43-0)

Guidance literature:

With hydrogenchloride; tert.-butyl lithium; In tetrahydrofuran; hexane;

upstream raw materials:

4-bromo-1H-indole

3-methoxycarbonylindole

4-bromo-1H-indole-3-carboxylic acid methyl ester

Trimethyl borate

Downstream raw materials:

methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-1H,1'H-2,4'-biindole-6-carboxylate

4-(3-bromo-5-nitro-phenyl)-1H-indole

AZ20

2-(4-fluorophenyl)-5-(1H-indol-4-yl)-N-methylbenzofuran-3-carboxamide

Refernces

• 1、 -. "GAMMA SECRETASE MODULATORS". Page/Page column 195-196. . Retrieved 2009/07/17.
• 2、 Hendrickson, James B.,Wang, Jian. "A New Synthesis of Lysergic Acid". . p. 3 - 5. Retrieved 2007/10/03.