642494-37-9

Basic information

• Product Name: Indole-7-boronic acid pinacol ester
• Synonyms: 1H-INDOL-7-YLBORONIC ACID PINACOL ESTER;7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE;INDOLE-7-BORONIC ACID PINACOL ESTER;1H-Indole-7-boronic acid, pinacol ester;REF DUPL: Indole-7-boronic acid pinacol ester;7-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1H-Indole, 7-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, 2-(1H-Indol-7-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 642494-37-9
• Molecular Formula: C₁₄H₁₈BNO₂
• Molecular Weight: 243.11
• Product Categories: Boronic ester;Indole;Organoborons
• Mol File: 642494-37-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: 94-96 °C
• Boiling Point: 396 °C at 760 mmHg
• Flash Point: 193.3 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 4.03E-06mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Keep Cold
• PKA: 17.01±0.30(Predicted)
• CAS DataBase Reference: Indole-7-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Indole-7-boronic acid pinacol ester(642494-37-9)
• EPA Substance Registry System: Indole-7-boronic acid pinacol ester(642494-37-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 642494-37-9(Hazardous Substances Data)

Usage

Uses

Indole-7-boronic acid, pinacol ester

InChI:InChI=1/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-7-5-6-10-8-9-16-12(10)11/h5-9,16H,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 70957-04-9 N-pivaloyl indole 
• 10294-33-4 boron tribromide 
• 2376879-92-2 2,2-dimethyl-1-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)propan-1-one 
• 120-72-9 indole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 919119-72-5 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole 
• 51417-51-7 7-bromo-1H-indole 
• 116491-57-7 2-trimethylsilanyl-1H-indole 
• 919119-70-3 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-trimethylsilanylindole 

Downstream Products

• 1863-21-4 7-(phenyl)-1H-indole 
• 1219637-86-1 7-cinnamylindole 
• 53924-05-3 7-chloro-1H-indole 
• 51417-51-7 7-bromo-1H-indole 
• 2380-84-9 7-Indolol 
• 52886-06-3 hippadine 

Relevant articles and documents

Suzuki–Miyaura Cross-Coupling Reactions of Tetrahydroxanthones and 4-Chromanone Lactones to Heteromeric Biaryls

We are reporting on a Suzuki–Miyaura cross-coupling study of a tetrahydroxanthone model system with different boronic acids, pinacolboranes, and halides to afford heteromeric biaryls. We transferred these reaction conditions to the Suzuki–Miyaura cross-coupling reactions of 4-chromanone lactones. We thereby obtained complex building blocks offering a convenient starting point for further transformations towards various natural products with the tetrahydroxanthone structural motif. (Figure presented.).

Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.

Metal-free directed sp 2-C–H borylation

Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials1. The discovery of simpler, milder and more efficient approaches to organoborons can