16732-69-7

Basic information

• Product Name: Ethyl 7-bromo-1H-indole-2-carboxylate
• Synonyms: 7-BROMOINDOLE-2-CARBOXYLIC ACID ETHYL ESTER;7-BROMO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER;ETHYL 7-BROMO-1H-INDOLE-2-CARBOXYLATE;ETHYL 7-BROMOINDOLE-2-CARBOXYLATE
• CAS NO: 16732-69-7
• Molecular Formula: C₁₁H₁₀BrNO₂
• Molecular Weight: 268.11
• Mol File: 16732-69-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 85-86 °C(Solv: ethanol (64-17-5))
• Boiling Point: 394.7 °C at 760 mmHg
• Flash Point: 192.5 °C
• Appearance: /
• Density: 1.554 g/cm³
• Vapor Pressure: 1.94E-06mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.35±0.30(Predicted)
• CAS DataBase Reference: Ethyl 7-bromo-1H-indole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 7-bromo-1H-indole-2-carboxylate(16732-69-7)
• EPA Substance Registry System: Ethyl 7-bromo-1H-indole-2-carboxylate(16732-69-7)

Safety Data

• Hazardous Substances Data: 16732-69-7(Hazardous Substances Data)

Usage

General Description

Ethyl 7-bromo-1H-indole-2-carboxylate is a chemical compound with the molecular formula C12H10BrNO2. It belongs to the class of organic compounds known as indole carboxylic acid esters and is commonly used in the field of pharmaceuticals and agrochemicals as a building block for the synthesis of various biologically active molecules. Ethyl 7-bromo-1H-indole-2-carboxylate is characterized by its indole ring structure, which is fused to a carboxylic acid ester group at the 2-position and a bromine atom at the 7-position. Ethyl 7-bromo-1H-indole-2-carboxylate has applications in drug discovery and development, specifically in the design and synthesis of potential drug candidates targeting specific biological pathways or molecular targets. Additionally, it is used as an intermediate in the production of various pharmaceutical and agrochemical products.

InChI:InChI=1/C11H10BrNO2/c1-2-15-11(14)9-6-7-4-3-5-8(12)10(7)13-9/h3-6,13H,2H2,1H3

Upstream product

• 18474-55-0 2-(2-bromo-phenylhydrazono)-propionic acid ethyl ester 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 50709-33-6 2-bromophenylhydrazine hydrochloride 
• 16732-66-4 2-bromophenylhydrazine 

Downstream Products

• 16732-71-1 7-bromo-1H-indole-2-carboxylic acid 
• 919119-62-3 ethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate 
• 53590-63-9 (7-bromo-1H-indol-2-yl)methanol 
• 1215384-46-5 (R)-7-[4-(3-dimethylamino-pyrrolidine-1-carbonyl)-piperazin-1-ylmethyl]-1-methyl-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide 

Relevant articles and documents

Synthesis, characterization, and catalytic application of palladium complexes containing indolyl-nnn-type ligands

In this study, a series of N-heterocyclic indolyl ligand precursors 2-Py-Py-IndH, 2-Py-Pz-IndH, 2-Py-7-Py-IndH, 2-Py-7-Pz-IndH, and 2-Ox-7-Py-IndH (L1H-L5H) were prepared. The treatment of ligand precursors with 1 equivalent of palladium acetate affords palladium complexes 1–5. All ligand precursors and palladium complexes were characterized by NMR spectroscopy and elemental analysis. The molecular structures of complexes 3 and 5 were determined by single crystal X-ray diffraction techniques. The application of those palladium complexes 1–5 to the Suzuki reaction with aryl halide substrates was examined.

Oxidative rearrangement of Indoles: A new approach to the EFHG-tetracyclic core of diazonamide A

(Chemical Equation Presented) A new approach to the ring EFHG-tetracyclic core fragment of the marine secondary metabolite diazonamide A is described. The route is based on the oxidative rearrangement of 3-arylindole-2-carboxylates. Thus, a range of 3-arylindole-2-carboxylates (3, 8) underwent rearrangement to the corresponding 3,3-disubstituted oxindoles (4, 9) with migration of the ester group upon treatment with tert-butyl hypochlorite followed by acid. The oxindoles 9 with a 3-[2-(4-methoxybenzyloxy)]phenyl substituent underwent cyclization to the tetracyclic aminals 11 following N-protection, reduction, and treatment with methanesulfonic anhydride. The methodology was applied to the tyrosine-indole derivative 17 to give the EFHG-tetracyclic core of diazonamide A.