777061-36-6

Basic information

• Product Name: 1-TERT-BUTOXYCARBONYLINDOLE-5-BORONIC ACID, PINACOL ESTER
• Synonyms: 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-BOC-INDOLE;1-(TERT-BUTYLOXY-CARBONYL)-INDOLE-5-BORONIC ACID PINACOL ESTER;1-TERT-BUTOXYCARBONYLINDOLE-5-BORONIC ACID, PINACOL ESTER;1-BOC-5-INDOLEBORONIC ACID PINACOL ESTER;TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLE-1-CARBOXYLATE;N-BOC-INDOLE-5-BORONIC ACID PINACOL ESTER;1-Boc-indole-5-boronic acid pinacol ester, 97%;1-Boc-5-indoleboronic acid pinacol ester, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-Boc-indole
• CAS NO: 777061-36-6
• Molecular Formula: C₁₉H₂₆BNO₄
• Molecular Weight: 343.23
• Product Categories: Heterocyclic Compounds;Boronic ester;Indole;Organoborons
• Mol File: 777061-36-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 131-136 °C(lit.)
• Boiling Point: 454.6°C at 760 mmHg
• Flash Point: 228.7°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 1.89E-08mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-TERT-BUTOXYCARBONYLINDOLE-5-BORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1-TERT-BUTOXYCARBONYLINDOLE-5-BORONIC ACID, PINACOL ESTER(777061-36-6)
• EPA Substance Registry System: 1-TERT-BUTOXYCARBONYLINDOLE-5-BORONIC ACID, PINACOL ESTER(777061-36-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 777061-36-6(Hazardous Substances Data)

Usage

General Description

1-Tert-butoxycarbonylindole-5-boronic acid, pinacol ester is a chemical compound with multiple functional groups. The "1-tert-butoxy" group is a protective group used in organic synthesis to protect the reactive indole ring, while the "5-boronic acid" group provides the compound with boron functionality, allowing for various reactions and applications. The pinacol ester group, on the other hand, confers stable and inert properties to the compound. This chemical can be used in organic chemistry as a building block for the synthesis of complex molecules and pharmaceuticals. It has potential applications in drug discovery and development due to its versatile and useful chemical properties.

InChI:InChI=1/C19H26BNO4/c1-17(2,3)23-16(22)21-11-10-13-12-14(8-9-15(13)21)20-24-18(4,5)19(6,7)25-20/h8-12H,1-7H3

Upstream product

• 374818-66-3 tert-butyl 5-iodo-1H-indole-1-carboxylate 
• 73183-34-3 bis(pinacol)diborane 
• 10075-50-0 5-bromo-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 188751-54-4 1-(tert-butoxycarbonyl)-1H-indole-5-carboxylic acid 
• 17422-32-1 5-chloro-1H-indole 
• 129822-48-6 tert-butyl 5-chloro-1H-indole-1-carboxylate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 317830-84-5 (1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid 
• 269410-24-4 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 182344-70-3 5-bromo-indole-1-carboxylic acid tert-butyl ester 

Downstream Products

• 1426095-25-1 N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-N-ethyl-4-(1H-indol-5-yl)benzamide 
• 1426095-29-5 N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide 
• 1426095-39-7 N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(phenylmethyl)benzamide 
• 1428884-69-8 potassium trifluoro(1-((tert-butoxy)carbonyl)-1H-indol-3-yl)boranuide 
• 1452507-32-2 discoipyrrole D 
• 1337933-00-2 C₂₅H₂₂N₂O₃S 
• 317830-84-5 (1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid 
• 1050440-92-0 1-(tert-butyloxycarbonyl)-1H-indol-5-ylpotassium trifluoroborates 
• 129822-47-5 tert‐butyl 5‐fluoroindole‐1‐carboxylate 
• 269410-24-4 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 

Relevant articles and documents

Gold-containing indoles as anticancer agents that potentiate the cytotoxic effects of ionizing radiation

This report describes the design and application of several distinct gold-containing indoles as anticancer agents. When used individually, all gold-bearing compounds display cytostatic effects against leukemia and adherent cancer cell lines. However, two gold-bearing indoles show unique behavior by increasing the cytotoxic effects of clinically relevant levels of ionizing radiation. Quantifying the amount of DNA damage demonstrates that each gold-indole enhances apoptosis by inhibiting DNA repair. Both Au(I)-indoles were tested for inhibitory effects against various cellular targets including thioredoxin reductase, a known target of several gold compounds, and various ATP-dependent kinases. While neither compound significantly inhibits the activity of thioreoxin reductase, both showed inhibitory effects against several kinases associated with cancer initiation and progression. The inhibition of these kinases provides a possible mechanism for the ability of these Au(I)-indoles to potentiate the cytotoxic effects of ionizing radiation. Clinical applications of combining Au(I)-indoles with ionizing radiation are discussed as a new strategy to achieve chemosensitization of cancer cells.

Copper-Photocatalyzed Borylation of Organic Halides under Batch and Continuous-Flow Conditions

The copper-photocatalyzed borylation of aryl, heteroaryl, vinyl and alkyl halides (I and Br) was reported. The reaction proceeded using a new heteroleptic Cu complex under irradiation with blue LEDs, giving the corresponding boronic-acid esters in good to excellent yields. The reaction was extended to continuous-flow conditions to allow an easy scale-up. The mechanism of the reaction was studied and a mechanism based on a reductive quenching (CuI/CuI*/Cu0) was suggested.

Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters

Herein, we report a conceptually novel borylation reaction proceeding via a mild photoinduced decarboxylation of redox-activated aromatic carboxylic acids. This work constitutes the first application of cheap and easily prepared N-hydroxyphthalimide esters as aryl radical precursors and does not require the use of expensive transition metals or ligands. The reaction is operationally simple, scalable, and displays broad scope and functional group tolerance.