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

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 778-82-5 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Pesticides1? ;Anti-inflammatory agents2? ;Antibacterial and antifungal agents? ;Anticonvulsant agents ? ;Hypotensive agents3? ;Analgesic agents4
2. 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.
3. Reactant for preparation of:PesticidesAnti-inflammatory agentsAntibacterial and antifungal agentsAnticonvulsant agents Hypotensive agentsAnalgesic agents

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

• 623-73-4 diazoacetic acid ethyl ester 
• 120-72-9 indole 
• 76367-43-6 ethyl 4,4-dimethoxybutyrate 
• 59-88-1 phenylhydrazine hydrochloride 
• 96296-38-7 3-ethoxycarbonylmethyl-indole-2-carboxylic acid 
• 111-46-6 diethylene glycol 
• 51079-10-8 ethyl 2-(1H-indol-3-yl)-2-oxoacetate 
• 7647-01-0 hydrogenchloride 
• 87-51-4 indole-3-acetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 879-37-8 3-indolylacetamide 
• 64-17-5 ethanol 
• 105-36-2 ethyl bromoacetate 
• 74-96-4 ethyl bromide 

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 
• 2591-98-2 indole-3-acetaldehyde 
• 4567-06-0 (2-phenyl-1H-indol-3-yl)acetic acid ethyl ester 
• 199593-80-1 1-Benzenesulfinyl-3-(1-benzenesulfonyl-2,3-dihydro-1H-indol-3-yl)-propan-2-ol 
• 199593-78-7 (1-benzenesulfonyl-3-indolinyl)methyl benzenesulfinylmethyl ketone 
• 199593-84-5 1-(1'-benzenesulfonyl-3'-indolinyl)-3-benzenesulfinyl-2-propyl acetate 
• 109986-85-8 ethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)indol-3-acetate 

Relevant articles and documents

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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.].

A new CDK2 inhibitor with 3-hydrazonoindolin-2-one scaffold endowed with anti-breast cancer activity: Design, synthesis, biological evaluation, and in silico insights

Background: Cyclin-dependent kinases (CDKs) regulate mammalian cell cycle progression and RNA transcription. Based on the structural analysis of previously reported CDK2 inhibitors, a new compound with 3-hydrazonoindolin-2-one scaffold (HI 5) was well designed, synthesized, and biologically evaluated as a promising anti-breast cancer hit compound. Methods: The potential anti-cancerous effect of HI 5 was evaluated using cytotoxicity assay, flow cytometric analysis of apoptosis and cell cycle distribution, ELISA immunoassay, in vitro CDK2/cyclin A2 activity, and molecular operating environment (MOE) virtual docking studies. Results: The results revealed that HI 5 exhibits pronounced CDK2 inhibitory activity and cytotoxicity in human breast cancer MCF-7 cell line. The cytotoxicity of HI 5 was found to be intrinsically mediated apoptosis, which in turn, is associated with low Bcl-2 expression and high activation of caspase 3 and p53. Besides, HI 5 blocked the proliferation of the MCF-7 cell line and arrested the cell cycle at the G2/M phase. The docking studies did not confirm which one of geometric isomers (syn and anti) is responsible for binding affinity and intrinsic activity of HI 5. However, the molecular dynamic studies have confirmed that the syn-isomer has more favorable binding interaction and thus is responsible for CDK2 inhibitory activity. Discussion: These findings displayed a substantial basis of synthesizing further derivatives based on the 3-hydrazonoindolin-2-one scaffold for favorable targeting of breast cancer.

Investigation of indole functionalized pyrazoles and oxadiazoles as anti-inflammatory agents: Synthesis, in-vivo, in-vitro and in-silico analysis

There are several potential side and adverse effects are found to be associated with the anti-inflammatory drugs in clinical practice. The long-term use of these clinical agents highly unsafe. It encouraged the development of novel heterocyclic compounds with potential anti-inflammatory activity and low to no toxicity. In present investigation, a total of 12 indole functionalized pyrazole and oxadiazole derivatives were designed, synthesized and evaluated for the in-vivo anti-inflammatory and analgesic potential. These compounds displayed comparable anti-inflammatory and analgesic potential to the reference drugs. Finally, molecular docking analysis was performed considering different anti-inflammatory targets to determine the mechanistic target of the designed molecules. Detailed analysis suggested that the molecules inhibit COX-2, preferably over other anti-inflammatory targets. The results suggested that two compounds (15c and 15f) were found promising candidates for the development of novel anti-inflammatory agents.