1912-33-0

Basic information

• Product Name: METHYL 3-INDOLYLACETATE
• Synonyms: (1H-Indole-3-yl)acetic acid methyl ester;Methyl 1H-Indole-3-acetate;INDOLE-3-ACETIC ACID METHYL ESTER(IAAMe);Methyl 2-(1H-indol-3-yl)acetate;2-(1H-indol-3-yl)acetic acid methyl ester;methyl 2-(1H-indol-3-yl)ethanoate;(1H-Indol-3-yl)-acetic acid methyl ester;Methyl β-Indoleacetate
• CAS NO: 1912-33-0
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.21
• EINECS: 217-622-5
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C11;Chemical Synthesis;Heterocyclic Building Blocks;Indoles;Indoles and derivatives;Heterocyclic Compounds
• Mol File: 1912-33-0.mol
• Article Data: 108

Chemical Properties

• Melting Point: 50-52 °C
• Boiling Point: 160-163 °C0.5 mm Hg
• Flash Point: 160.5 °C
• Appearance: Dark brown oil
• Density: 1.223
• Vapor Pressure: 7.86E-05mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 16.66±0.30(Predicted)
• BRN: 158031
• CAS DataBase Reference: METHYL 3-INDOLYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-INDOLYLACETATE(1912-33-0)
• EPA Substance Registry System: METHYL 3-INDOLYLACETATE(1912-33-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1912-33-0(Hazardous Substances Data)

Usage

Description

METHYL 3-INDOLYLACETATE, also known as the methyl ester of indole-3-acetic acid, is a phytohormone derived from the indole-3-acetic acid. It is characterized by its dark brown oil appearance and possesses unique chemical properties that make it suitable for various applications across different industries.

Uses

Used in Agricultural Industry:
METHYL 3-INDOLYLACETATE is used as a plant growth regulator for promoting plant growth and development. Its role as a phytohormone allows it to influence various aspects of plant growth, such as cell division, elongation, and differentiation, leading to improved crop yields and quality.
Used in Pharmaceutical Industry:
METHYL 3-INDOLYLACETATE is used as a precursor in the synthesis of various pharmaceutical compounds. Its unique chemical structure makes it a valuable building block for the development of new drugs with potential applications in treating various medical conditions.
Used in Chemical Research:
METHYL 3-INDOLYLACETATE serves as an important research compound in the field of organic chemistry. Its chemical properties and reactivity make it a useful tool for studying various chemical reactions and mechanisms, contributing to the advancement of scientific knowledge in this area.
Used in Cosmetics Industry:
METHYL 3-INDOLYLACETATE is used as an active ingredient in some cosmetics and personal care products. Its potential benefits for skin health and its ability to regulate cellular processes make it a valuable addition to formulations aimed at improving skin appearance and function.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 6817, 1992 DOI: 10.1021/jo00051a027Tetrahedron Letters, 22, p. 1475, 1981 DOI: 10.1016/S0040-4039(01)90354-5Tetrahedron, 39, p. 3767, 1983 DOI: 10.1016/S0040-4020(01)88618-X

InChI:InChI=1/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 87-51-4 indole-3-acetic acid 
• 73930-45-7 3-[(E)-octa-2,7-dienyl]-1H-indole 
• 120-72-9 indole 
• 5199-50-8 methyl 2-iodoacetate 
• 67-56-1 methanol 
• 85676-99-9 (2,3-dihydroindol-3-yl)acetic acid methyl ester 
• 17697-12-0 benzeneseleninic anhydride 
• 19077-78-2 Methyl 4-chloro-3-indoleacetate 
• 156049-34-2 (E)-methyl 3-(2-isocyanophenyl)acrylate 
• 136788-88-0 methyl 1-hydroxyindole-3-acetate 
• 174319-54-1 methyl 3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate 
• 74-88-4 methyl iodide 
• 485-80-3 S-adenosyl-L-methionine 

Downstream Products

• 858232-60-7 bis-(3-methoxycarbonylmethyl-indol-2-yl)-phenyl-methane 
• 101792-67-0 2-(1H-indol-3-yl)-N-phenethyl acetamide 
• 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 
• 73031-14-8 2-(1H-indol-3-yl)-N-benzyl acetamide 
• 73857-27-9 methyl 3-indolylbenzoylacetate 
• 113975-70-5 methyl α-(phenylmethyl)indole-3-acetate 
• 91361-01-2 <4-Dimethylaminophenyl>-bis-<3-(2-methoxyacetyl)-indol-2-yl>-methan 
• 132906-25-3 N_b-Methyl-3-indoleacetamide 
• 58665-00-2 (1-methyl-1H-indol-3-yl)acetic acid methyl ester 
• 2591-98-2 indole-3-acetaldehyde 
• 70625-87-5 methyl 2-(formamidobenzoyl)acetate 

Relevant articles and documents

Construction of indole and benzofuran systems on the solid phase via palladium-mediated cyclizations

Molecular diversity in the area of nonpeptide, small organic molecules has been receiving considerable attention in the chemical community. Herein, we report new solid-phase methodology for the rapid generation of such small-molecule libraries by simultaneous-parallel or combinatorial synthesis. We have adapted a palladium-mediated, intramolecular Heck-type reaction, a mild and versatile method for carbon-carbon bond formation, to the solid phase. This has been applied to the synthesis of diverse indole and benzofuran derivatives, such as 8, 15, and 28, in good to excellent yields.

Reconsidering the Structure of Serlyticin-A

Serlyticin-A is a secondary metabolite first isolated from a culture of Serratia ureilytica grown using squid pen as the sole carbon/nitrogen source. A previous study by Kuo et al. demonstrated that it has antioxidative and antiproliferative properties. However, the proposed chemical structure of serlyticin-A is likely incorrect based on the thermodynamic instability of its three contiguous heteroatom-heteroatom bonds. Here, we use quantum chemical calculations to predict 1H and 13C chemical shifts for serlyticin-A and demonstrate a discrepancy between the calculated and experimental chemical shifts. We then propose several reasonable alternative structures for serlyticin-A. Considering the known antioxidant and antiproliferative activity of hydroxamic acids as well as their stability and prevalence in natural products of bacterial origin, we believe that serlyticin-A is most likely 3-indolylacetohydroxamic acid (4). We provide our rationale for this assignment as well as experimental data for pure 3-indolylacetohydroxamic acid obtained via de novo synthesis. This study highlights the power of computational NMR shift prediction to revise chemical structures for natural products like serlyticin-A.

Reaction of methyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate with ureas: Facile entry into the polycyclic meridianin analogues with uracil structural unit

Methyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate was prepared simply and efficiently in two steps from 3-indoleacetic acid employing N,N-dimethylformamide dimethylacetal (DMFDMA). Upon treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate with various (thio)ureas in the presence of an acid 2-(1H-indol-3-yl)-3-(3-substituted(thio)ureido) propenoates were obtained in high yields. A base promoted cyclization of these (thio)ureidopropenoate derivatives afforded 5-(indol-3-yl)-3-substituted- pyrimidine-2,4-diones which represent a new family of meridianine analogues.

QUANTIFICATION OF INDOL-3-YL ACETIC ACID IN PEA AND MAIZE SEEDLINGS BY GAS CHROMATOGRAPHY-MASS SPECTROMETRY

A procedure is described for the identification and quantification of IAA in plant tissues by GC/MS analysis of the N-heptafluorobutyryl ethyl ester of IAA using IAA as an internal standard.The detection limit is ca. 3 pmol IAA/tissue sample.By using this method, IAA levels of 30-90 pmol/g fr. wt were obtained for dark-grown Pisum sativum epicotyls and 71-199 pmol/g fr. wt for dark-grown Zea mays seedlings.When either methanol or ethanol was used as extraction solvent, some esterification of IAA during sample preparation was observed.No evidence for the natural occurence of methyl or ethyl esters of IAA in Pisum sativum seedlings was found.Key Word Index-Pisum sativum; Zea mays; Leguminosae; Gramineae; hormone; indol-2-yl acetic acid; GC/MS; deuterium label.

Discovery of an indole-substituted furanone with tubulin polymerization inhibition activity

Analogs of diarylpyrrolinone lead compound 1 were prepared and tested for anti-proliferative activity in U-937 cancer cells. Alterations of 1 focused on modifying the two nitrogen atoms: a) the pyrrolinone nitrogen atom was substituted with a propyl group or replaced with an oxygen atom (furanone), and b) the substituents on the indole nitrogen were varied. These changes led to the discovery of a furanone analog 3b with sub-micromolar anti-cancer potency and tubulin polymerization inhibition activity.

Etude spectroscopique (IR, RMN1H, masse) comparee des acides indolyl-1 acetique (AIA-1) indolyl-2 acetique (AIA-2) et indolyl-3 acetique (AIA-3) et de leurs esters methyliques (masse)

Spectroscopic study (i.r., PMR) of 1-indolyl, 2-indolyl and 3-indolyl acetic acids points out structural differences.Conventional mass spectra of the three acids or their methyl esters are very similar.Use of the MIKE and CID-MIKE techniques on the molecular ion allows an easy discrimination of each methylic ester of the three acids.

Identification of organophosphorus simulants for the development of next-generation detection technologies

Organophosphorus (OP) chemical warfare agents (CWAs) represent an ongoing threat but the understandable widespread prohibition of their use places limitations on the development of technologies to counter the effects of any OP CWA release. Herein, we describe new, accessible methods for the identification of appropriate molecular simulants to mimic the hydrogen bond accepting capacity of the PO moiety, common to every member of this class of CWAs. Using the predictive methodologies developed herein, we have identified OP CWA hydrogen bond acceptor simulants for soman and sarin. It is hoped that the effective use of these physical property specific simulants will aid future countermeasure developments.

Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer

Fe, Co, and Mn hydride-initiated radical olefin additions have enjoyed great success in modern synthesis, yet the extension of other hydrogen radicalophiles instead of olefins remains largely elusive. Herein, we report an efficient Fe-catalyzed intramolec