144104-59-6

Basic information

• Product Name: 5-Indolylboronic acid
• Synonyms: 1H-INDOLE-5-BORONIC ACID;1H-INDOL-5-YLBORONIC ACID;5-INDOLYLBORONIC ACID;5-INDOLEBORONIC ACID;AKOS BRN-0120;INDOLE-5-BORONIC ACID;RARECHEM AH PB 0158;5-Indole Boric Acid
• CAS NO: 144104-59-6
• Molecular Formula: C₈H₈BNO₂
• Molecular Weight: 160.97
• Product Categories: blocks;BoronicAcids;IndolesOxindoles;Indoles and derivatives;Boronic acids;Heterocyclic Compounds;Boronic acid;Indole;Organoborons
• Mol File: 144104-59-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 170-175 °C
• Boiling Point: 433.2 °C at 760 mmHg
• Flash Point: 215.8 °C
• Appearance: White/Crystalline Powder
• Density: 1.33 g/cm³
• Vapor Pressure: 2.83E-08mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: 0-6°C
• PKA: 8.91±0.30(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 5-Indolylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Indolylboronic acid(144104-59-6)
• EPA Substance Registry System: 5-Indolylboronic acid(144104-59-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-21/22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 144104-59-6(Hazardous Substances Data)

Usage

Description

5-Indolylboronic acid is a white to light yellow crystalline powder that may contain varying amounts of anhydride. It is a versatile reagent in organic chemistry, particularly in palladium and copper-catalyzed oxidative cross-coupling reactions.

Uses

1. Used in Pharmaceutical Industry:
5-Indolylboronic acid is used as a reactant for the synthesis of biologically active molecules for various therapeutic applications.
2. Used in Arthritis Treatment:
5-Indolylboronic acid is used as a reactant in the synthesis of indole inhibitors of MMP-13, which are potential treatments for arthritic diseases.
3. Used in Anticancer Applications:
5-Indolylboronic acid is used as a reactant in the synthesis of substituted pyrimidines, which act as tubulin polymerization inhibitors and have potential applications in cancer treatment.
4. Used in Suzuki Coupling Reactions:
5-Indolylboronic acid is used as a reactant in Suzuki coupling reactions for the synthesis of aryl-hetarylfurocoumarins, aryl-substituted oxabenzindoles, and methanobenzindoles, which are compounds with potential biological activities.
5. Used in Organic Synthesis:
5-Indolylboronic acid is used as a useful reagent for palladium and copper-catalyzed oxidative cross-coupling of mercaptoacetylenes and arylboronic acids, as well as in trifluoromethylation reactions, contributing to the synthesis of a wide range of organic compounds.

InChI:InChI=1/C8H8BNO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10-12H

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 688-74-4 boric acid tributyl ester 
• 5419-55-6 Triisopropyl borate 
• 13675-18-8 tetrahydroxydiboron 

Downstream Products

• 128373-22-8 5-(furan-2-yl)-1H-indole 
• 144104-54-1 5-(thiophen-2-yl)-1H-indole 
• 144104-53-0 5-(furan-3-yl)-1H-indole 
• 152920-53-1 5-(thiophen-3-yl)-1H-indole 
• 117908-10-8 5-(2-pyridyl)indole 
• 144104-49-4 5-(pyridin-3-yl)-1H-indole 
• 66616-72-6 5-phenyl-1H-indole 
• 144104-46-1 5-(4-methoxyphenyl)-1H-indole 
• 90679-35-9 5-(4-pyridyl)indole 
• 144104-45-0 5-(2-methoxyphenyl)indole 
• 144104-44-9 5-(4-fluoro-phenyl)-1H-indole 
• 210888-94-1 3-(1H-indol-5-yl)benzaldehyde 
• 1037364-92-3 4-(1H-indol-5-yl)-benzoic acid ethyl ester 
• 694533-08-9 4-(1H-indol-5-yl)-benzonitrile 

Relevant articles and documents

Conjugated oligomers with thiophene and indole moieties: Synthesis, photoluminescence and electrochromic performances

Two series of thiophene oligomers and terthiophene oligomers consisting of both thiophene and indole moieties have been synthesized. They have same excitation-dependent photoluminescence characteristics, but different bandgaps and absorption behaviors, which relates to the number and denseness of indoles in the conjugated oligomers and the length of alkyl chains on indole moiety due to varied the π-π stacking interaction of conjugated structures in the as-prepared oligomers. A simple electrochromic device based on such a conjugated oligomer displays a novel four-color electrochromism from red to yellow, green and puce with the increased potential and possesses good environmental and redox stability. Such conjugated oligomer also exhibits high sensitivity and selectivity for Zn2+detection.

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: One step greener

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N) 2B-B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B 2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.