15591-70-5

Basic information

• Product Name: methyl 4-(indol-3-yl)butyrate
• Synonyms: methyl 4-(indol-3-yl)butyrate;1H-Indole-3-butanoic acid methyl ester;1H-Indole-3-butyric acid methyl ester;Indole-3-butyric acid methyl ester;Methyl indole-3-butyrate;INDOLE-3-BUTYRIC ACIDMETHYL ESTER (IBAMe);METHYL 3-INDOLEBUTYRATE;Methyl 4-(1H-indol-3-yl)butanoate
• CAS NO: 15591-70-5
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.2637
• EINECS: 239-658-0
• Mol File: 15591-70-5.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 382.3°C at 760 mmHg
• Flash Point: 185°C
• Appearance: /
• Density: 1.157g/cm³
• Vapor Pressure: 4.79E-06mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: methyl 4-(indol-3-yl)butyrate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(indol-3-yl)butyrate(15591-70-5)
• EPA Substance Registry System: methyl 4-(indol-3-yl)butyrate(15591-70-5)

Safety Data

• Hazardous Substances Data: 15591-70-5(Hazardous Substances Data)

Usage

Description

Methyl 4-(indol-3-yl)butyrate, also known as Indole-3-butyric Acid Methyl Ester, is an organic compound derived from the indole family. It is characterized by its unique chemical structure, which features an indole ring and a butyrate ester group. methyl 4-(indol-3-yl)butyrate is known for its potential applications in various fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
Methyl 4-(indol-3-yl)butyrate is used as a reactant for the synthetic preparation of 4-[4-(1H-indol-3-yl)butyl]piperazine, a common precursor in the development of pharmaceutical compounds. This application is due to its ability to serve as a building block for the synthesis of various drugs, potentially contributing to the creation of new medications with diverse therapeutic effects.

InChI:InChI=1/C13H15NO2/c1-16-13(15)8-4-5-10-9-14-12-7-3-2-6-11(10)12/h2-3,6-7,9,14H,4-5,8H2,1H3

Upstream product

• 1022576-81-3 ethyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate 
• 67-56-1 methanol 
• 100116-53-8 5-(2-amino-phenyl)-6-chloro-hex-5-enoic acid 
• 550-71-0 6-chloromethylene-3,4,5,6-tetrahydro-1H-benz[b]azocin-2-one 
• 2047-91-8 2,3-dihydro-1H-cyclopentindole 
• 133-32-4 4-indol-3-yl-butyric acid 
• 74-88-4 methyl iodide 
• 818-57-5 Methyl 4-pentenoate 
• 201230-82-2 carbon monoxide 
• 100-63-0 phenylhydrazine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 180910-58-1 methyl 1-hydroxyindole-3-butylate 
• 186581-53-3 diazomethane 

Downstream Products

• 3364-37-2 4-(1H-indol-3-yl)butan-1-ol 
• 21903-93-5 4-(1H-indol-3-yl)butyl 4-methylbenzenesulfonate 
• 1169708-30-8 methyl 4-(1-(3-methoxyphenyl)-1H-indol-3-yl)-butanoate 
• 1169708-29-5 methyl 4-(1-phenyl-1H-indol-3-yl)-butanoate 
• 1166184-86-6 methyl 4-(1-benzyl-1H-indol-3-yl)butanoate 
• 6245-89-2 Homotryptamine 
• 4281-79-2 3-{4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-indole 
• 147817-50-3 siramesine 

Relevant articles and documents

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Synthesis, spectral analysis and in vitro cytotoxicity of diorganotin (IV) complexes derived from indole-3-butyric hydrazide

A series (1–20) of diorganotin (IV) complexes with general formula R2SnL were formed by the reaction of R2SnCl2 (where R = Me, Et, Bu and Ph) with Schiff base ligands (H2L1–4) derived from the reaction of indole-3-butyric hydrazide with the salicylaldehyde and its derivatives. The structure elucidation of compounds were done by using UV–Vis, FT-IR, NMR (1H, 13C, 119Sn), Mass spectrometry and thermal gravimetric analysis. Spectroscopic evidences suggested tridentate nature (ONO) of Schiff base ligands and coordinated to the dialkyl/diaryltin (IV) moieties through nitrogen and oxygen donor sites giving pentacoordinated geometry to complexes. The compounds were tested for the antimicrobial activity against bacterial and fungal strains which showed promising biological activity with compound 20 (Ph2SnL4) as most active against microbes. The in silico study of the compounds was carried and observed that the compounds are used as orally active drugs and promote the formation of different hydrazide based drugs. The synthesized compounds were tested against human carcinoma cell lines namely A549, MCF7 and one normal cell line IMR 90 using MTT assay. The diethyl and dibutyltin complexes of Schiff bases displayed good cytotoxic activities. Compound 3 (H2L3) and 10 (Et2SnL2) were most potent against cancer cell lines with lowest IC50 values and 7–8 times less toxic against the normal cell line.

Synthesis of Various Bridged Ring Systems via Rhodium-Catalyzed Bridged (3+2) Cycloadditions

Here, we describe the rhodium-catalyzed bridged (3+2) cycloaddition cascade reactions of N-sulfonyl-1,2,3-triazoles, which allowed the efficient diastereoselective construction of various functionalized and synthetically challenging bridged ring systems. This simple, direct transformation had a broad substrate scope and excellent functional group tolerance. The highly strained polycyclic bicyclo[2.2.2]octa[b]indole core of fruticosine was synthesized efficiently using this methodology.

A double-indole hydrazone compound and use thereof

The invention provides a bisindole acylhydrazone compound shown as the formula I or salt, hydrate or crystals, accepted in the pharmacy, of the bisindole acylhydrazone compound. According to the bisindole acylhydrazone compound, R does not exist or is selected from alkylene of C1-5. The bisindole acylhydrazone compound has a certain antibacterial activity, and can serve as potential antibiotics or a daily chemical product. What is beyond the expectation is that compounds 4e-4h and compounds 4a-4c are quite similar in structure, the antibacterial activity of the compounds 4e-4h and the antibacterial activity of the compounds 4a-4c are obviously better than that of other compounds, particularly, the activity of the compound 4h is best and is remarkably better than that of compounds 4e-4g. The formula I is shown in the specification.