778-82-5

Basic information

• Product Name: Ethyl 3-indoleacetate
• Synonyms: IAA ETHYL ESTER;INDOLE-3-ACETIC ACID ETHYL ESTER;ETHYL 3-INDOLACETATE;ETHYL 3-INDOLEACETATE;ethyl indol-3-ylacetate;ETHYL INDOLE-3-ACETATE;3-INDOLYL-ACETIC ACID-ETHYL ESTER;1h-indole-3-acetic acid ethyl ester
• CAS NO: 778-82-5
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• EINECS: 212-296-0
• Product Categories: Indoles and derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;C12;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 778-82-5.mol
• Article Data: 42

Chemical Properties

• Melting Point: 44-45 °C(lit.)
• Boiling Point: 164-166 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Crystalline Powder
• Density: 1.1255 (rough estimate)
• Vapor Pressure: 3.59E-05mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: -20°C
• Solubility: soluble in Methanol
• PKA: 16.70±0.30(Predicted)
• Water Solubility: insoluble
• BRN: 171682
• CAS DataBase Reference: Ethyl 3-indoleacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-indoleacetate(778-82-5)
• EPA Substance Registry System: Ethyl 3-indoleacetate(778-82-5)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-21/22
• Safety Statements: 36/37/39-26-24/25
• WGK Germany: 3
• RTECS: NL3528000
• Hazardous Substances Data: 778-82-5(Hazardous Substances Data)

Usage

Description

Ethyl 3-indoleacetate is a white crystalline powder that serves as a versatile chemical intermediate and reactant in the synthesis of various pharmaceutical agents and compounds.

Uses

Used in Pharmaceutical Industry:
Ethyl 3-indoleacetate is used as a reactant for the preparation of several pharmaceutical agents, including:
1. Pesticides: It is used in the development of pesticides to control and eliminate pests.
2. Anti-inflammatory agents: It is utilized in the synthesis of anti-inflammatory drugs to reduce inflammation and alleviate pain.
3. Antibacterial and antifungal agents: It serves as a reactant in the production of antibacterial and antifungal medications to combat bacterial and fungal infections.
4. Anticonvulsant agents: Ethyl 3-indoleacetate is used in the preparation of anticonvulsant drugs to treat seizures and epilepsy.
5. Hypotensive agents: It is employed in the synthesis of hypotensive medications to lower blood pressure and manage hypertension.
6. Analgesic agents: It is used in the production of analgesics to relieve pain and discomfort.
Used in Organic Synthesis:
Ethyl Indole-3-acetate is a compound used in the synthesis of 9H-Pyrrolo[1,2-α]Indoles via Michael Addition-Condensation with α,β-Unsaturated Ketimines, contributing to the development of novel chemical compounds and materials.

InChI:InChI=1/C12H13NO2/c1-2-15-12(14)7-9-8-13-11-6-4-3-5-10(9)11/h3-6,8,13H,2,7H2,1H3

Upstream product

• 18443-04-4 3-indolylacetic acid ethyl imido ester hydrochloride 
• 31529-27-8 2-carboxy-3-indoleacetic acid 
• 120-72-9 indole 
• 105-36-2 ethyl bromoacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 74-96-4 ethyl bromide 
• 87-51-4 indole-3-acetic acid 
• 879-37-8 3-indolylacetamide 
• 64-17-5 ethanol 
• 19213-72-0 ethyl 1-imidazolecarboxylate 
• 771-51-7 indole-3-acetonitrile 
• 105-39-5 chloroacetic acid ethyl ester 
• 7647-01-0 hydrogenchloride 
• 51079-10-8 ethyl 2-(1H-indol-3-yl)-2-oxoacetate 

Downstream Products

• 526-55-6 2-(3-indole)-ethanol 
• 87-51-4 indole-3-acetic acid 
• 879-37-8 3-indolylacetamide 
• 5448-47-5 1H-indol-3-acetohydrazide 
• 58827-74-0 N-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-2-(1H-indol-3-yl)-acetamide 
• 104777-75-5 (+/-)-2-<(3RS,4SR)-N-benzyloxycarbonyl-3-ethyl-4-piperidylacetyl>-3-ethoxycarbonylmethylindole 
• 56999-62-3 ethyl 2-(1-methyl-1H-indol-3-yl)acetate 
• 199593-76-5 ethyl (1-benzenesulfonyl-3-indolinyl)acetate 
• 221188-34-7 [1-(4-fluoro-phenyl)-1H-indol-3-yl]-acetic acid ethyl ester 
• 221188-35-8 [1-(4-fluoro-benzyl)-1H-indol-3-yl]-acetic acid ethyl ester 
• 2591-98-2 indole-3-acetaldehyde 
• 1912-37-4 (2-bromo-1H-indol-3-yl)-acetic acid ethyl ester 
• 2597-26-4 2-(1H-Indol-3-yl)-propionic acid 
• 738608-57-6 2-(2-benzoyl-1H-indol-3-yl)-pentan-3-one 

Relevant articles and documents

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Discovery, synthesis and biological characterization of a series of: N -(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1 H -pyrazol-5-yl)acetamide ethers as novel GIRK1/2 potassium channel activators

The present study describes the discovery and characterization of a series of N-(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1H-pyrazol-5-yl)acetamide ethers as G protein-gated inwardly-rectifying potassium (GIRK) channel activators. From our previous lead optimization efforts, we have identified a new ether-based scaffold and paired this with a novel sulfone-based head group to identify a potent and selective GIRK1/2 activator. In addition, we evaluated the compounds in tier 1 DMPK assays and have identified compounds that display nanomolar potency as GIRK1/2 activators with improved metabolic stability over the prototypical urea-based compounds. This journal is

SUBSTITUTED TETRAHYDROPYRANOINDOLES, DERIVATIVES THEREOF, AND THEIR METHODS OF SYNTHESIS AND USE

Disclosed herein are tetrahydropyranoindole compounds and derivatives thereof, as well as their methods of synthesis and use. The disclosed compounds may be synthesized by methods that utilize a cooperative hydrogen bond donor/Br?nsted acid system. The disclosed compounds may be useful for treating a disease, disorder, or a symptom thereof in a subject in need thereof, such as pain, swelling, and joint stiffness. The disclosed compounds also may be useful for treating cell proliferative diseases and disorders such as cancer.

Diversity-oriented synthesis and antifungal activities of novel pimprinine derivative bearing a 1,3,4-oxadiazole-5-thioether moiety

Abstract: Based on the strategy of diversity-oriented synthesis and the structures of natural product pimprinine and streptochlorin, two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties were efficiently synthesized under the optimized reaction conditions. Biological assays conducted at Syngenta showed the designed derivatives displayed an altered pattern of biological activity, of which 5h was identified as the most promising compound with strong activity against Pythium dissimile and also a broad antifungal spectrum in primary screening. Further structural optimization of pimprinine and streptochlorin derivatives is well under way, aiming to discover synthetic analogues with improved antifungal activity. Graphic abstract: Two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties wereefficiently synthesized through diversity-oriented synthesis strategy under the optimizedconditions. Biological assays showed the designed derivatives exhibited potential activity.[Figure not available: see fulltext.].