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

• 51417-51-7 7-bromo-1H-indole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 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 
• 919119-72-5 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-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.).

Preparation method of indole type or aniline type borate

The invention discloses a preparation method of indole type or aniline type borate, which comprises the following step: reacting an indole type raw material or aniline type raw material with boron trihalide in an organic solvent under the protection of in

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.