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

Uses

Indole-3-butyric Acid Methyl Ester is a reactant used in the synthetic preparation of the common precursor, 4-[4-(1H-indol-3-yl)butyl]piperazine.

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

• 186581-53-3 diazomethane 
• 133-32-4 4-indol-3-yl-butyric acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 550-71-0 6-chloromethylene-3,4,5,6-tetrahydro-1H-benz[b]azocin-2-one 
• 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 
• 74-88-4 methyl iodide 
• 818-57-5 Methyl 4-pentenoate 
• 201230-82-2 carbon monoxide 
• 100-63-0 phenylhydrazine 
• 180910-58-1 methyl 1-hydroxyindole-3-butylate 
• 2047-91-8 2,3-dihydro-1H-cyclopentindole 

Downstream Products

• 163631-03-6 4-(1-benzyl-1H-indol-3-yl)-1-butanol 
• 143682-52-4 3-[4-(4-phenyl-1-piperidyl)-butyl]-indole 
• 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 
• 4281-79-2 3-{4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-indole 
• 147817-50-3 siramesine 
• 163630-97-5 4-<1-(4-fluorophenyl)-1H-indol-3-yl>-1-butanol methanesulfonate ester 

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.

Method for synthesizing 3-hydroxyl oxoindole derivative

The invention discloses a method for synthesizing a 3-hydroxyl oxoindole derivative. The synthetic route is as shown in the specification, wherein R1 is methyl, ethyl, propyl, butyl, isopropyl, cyclohexyl, allyl, benzyloxyethyl or n-butyric acid methyl ester; a substituent R2 is methyl, methoxy, benzyloxy, fluorine, chlorine or bromine; and a substituent R3 is methyl, bromine or phenyl. The synthetic process comprises the following steps: dissolving a compound I and iodobenzene diacetate in acetic acid and reacting completely at 40-100 DEG C, and postprocessing and purifying to obtain a product II. The raw materials used in the method are easy to prepare, and iodobenzene diacetate can be sold in the market; there is no need to use a catalyst such as a metal catalyst or an organic catalyst, and cost is reduced and the method is environment-friendly.