1912-48-7

Basic information

• Product Name: 1-METHYL-3-INDOLEACETIC ACID
• Synonyms: (1-METHYL-1H-INDOL-3-YL)ACETIC ACID;1-METHYL-3-INDOLEACETIC ACID;1-METHYLINDOLE-3-ACETIC ACID;2-(1-METHYL-1H-INDOL-3-YL)ACETIC ACID;IFLAB-BB F1920-0023;RARECHEM AH BS 0119;1-METHYL-3-INDOLEACETIC ACID 98%;1-METHYLINDOLE-3-ACETIC ACID 98% (HPLC)
• CAS NO: 1912-48-7
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 1912-48-7.mol

Chemical Properties

• Melting Point: 126-128 °C(lit.)
• Boiling Point: 392 °C at 760 mmHg
• Flash Point: 190.9 °C
• Appearance: White to tan/Crystalline Powder
• Density: 1.2 g/cm³
• Vapor Pressure: 7.56E-07mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• PKA: 4.53±0.30(Predicted)
• CAS DataBase Reference: 1-METHYL-3-INDOLEACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-3-INDOLEACETIC ACID(1912-48-7)
• EPA Substance Registry System: 1-METHYL-3-INDOLEACETIC ACID(1912-48-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1912-48-7(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-METHYL-3-INDOLEACETIC ACID is used as a reactant for the enantioselective preparation of α-aryl alkylcarboxylic acids, which are important in the development of pharmaceutical compounds.
2. Used in Protein Kinase C Imaging:
1-METHYL-3-INDOLEACETIC ACID is used as a reactant for the preparation of PKC inhibitor methylindolylpyridinylmethylpiperidinylindolylpyrroledione, which is utilized in protein kinase C imaging.
3. Used in Synthesis of Bioactive Compounds:
1-METHYL-3-INDOLEACETIC ACID is used as a reactant for stereoselective preparation of δ-lactones via Michael addition/lactonization with unsaturated carboxylates, which are essential in the synthesis of various bioactive compounds.
4. Used in Anticancer Drug Synthesis:
1-METHYL-3-INDOLEACETIC ACID is used as a reactant for stereoselective preparation of vindorosine, vindoline, and analogs, which are known for their anticancer properties.
5. Used in Antiangiogenic and Protein Kinase Inhibition:
1-METHYL-3-INDOLEACETIC ACID is used as a reactant for the preparation of (indolyl)pyrrol-2-ones, which serve as VEGF-R inhibitors, antiangiogenic agents, and protein kinase inhibitors.
6. Used in Antifungal Agent Synthesis:
1-METHYL-3-INDOLEACETIC ACID is used as a reactant for the synthesis of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues, which exhibit antifungal properties.
7. Used in Plant Growth Regulation:
1-METHYL-3-INDOLEACETIC ACID is used as a plant growth regulator due to its activity as a natural auxin, which plays a crucial role in the growth and development of plants.

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

Upstream product

• 56999-62-3 ethyl 2-(1-methyl-1H-indol-3-yl)acetate 
• 87-51-4 indole-3-acetic acid 
• 74-88-4 methyl iodide 
• 126775-00-6 N-ethylindol-3-yl acetic acid-methyl ester 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 58665-00-2 (1-methyl-1H-indol-3-yl)acetic acid methyl ester 
• 58664-93-0 2-carboxy-1-methyl-3-indoleacetic acid 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 19012-02-3 N-methyl-3-acetylindole 
• 84670-23-5 1-Methyl-3-phenylcarbamoylmethyl-1H-indole-2-carboxylic acid 
• 60442-30-0 1,3-dioxo-9-methyl-1H,3H,4H,9H-indolo<2,3-c>pyran 
• 778-82-5 ethyl 3-indoleacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 94575-23-2 1-Methyl-3-(N-phenylcarbamoylmethyl)-1H-indole 

Downstream Products

• 875-30-9 1,3-dimethylindole 
• 609843-63-2 3-(1-methylindol-3-yl)-4-[1-(2-deoxy-3,4-di-O-p-toluyl-β-D-ribofuranosyl)indol-3-yl]furan-2,5-dione 
• 909568-46-3 N-(2-bromo-4-methylphenyl)-2-(1-methyl-1H-indol-3-yl)acetamide 
• 58665-00-2 (1-methyl-1H-indol-3-yl)acetic acid methyl ester 
• 150114-41-3 1-methylindole-3-acetamide 
• 1218935-78-4 C₃₁H₃₆N₄O₇ 
• 1267588-46-4 (3R,4R)-methyl 3-(1-methyl-1H-indol-3-yl)-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate 
• 1313038-73-1 2-(1-methyl-1H-indol-3-yl)-N-(3-{[5-(phenylcarbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}phenyl)acetamide 
• 1350638-03-7 C₁₈H₁₆ClNO₂ 
• 1350637-99-8 methyl 2-(2-phenyl-1-methyl-1H-indol-3-yl)acetate 
• 1350638-02-6 C₁₉H₁₉NO₃ 
• 1350638-05-9 C₂₁H₂₁NO₄ 
• 1350638-00-4 (1-methyl-2-p-tolyl-1H-indol-3-yl)acetic acid methyl ester 
• 1350638-10-6 C₁₉H₁₉NO₂ 

Relevant articles and documents

Synthesis of N-alkyl substituted bioactive indolocarbazoles related to G?6976

The syntheses of new nitrile and amide analogues of 7-keto G?6976 are described. The amide analogue 22 was formed via the condensation with a new functionalized indoleacetic acid derivative 25 to overcome the solubility problem during the coupling reaction.

Thee-component, one-pot synthesis of hexahydroazepino[3,4-b]indole and tetrahydro-1H-pyrido[3,4-b]indole derivatives and evaluation of their cytotoxicity

A three-component, four-center Ugi reaction has been developed to produce a novel class of 2-aryl-3-oxo-hexahydroazepino[3,4-b]indole and 2-aryl-3-oxo-tetrahydro-1H-pyrido[3,4-b]indole derivatives in good to high yields. A few of them exhibit moderate cyt

Synthesis of 7-keto-Goe6976 (ICP-103)

An efficient synthesis of 7-keto-Goe6976 (ICP-103) (3) is described that employs palladium(II) inflate in the final oxidative cyclization step.

Total Synthesis of Na-Methylsecodine

A short synthetic route to Na-methylsecodine is described involving a Friedel-Crafts acylation at the indole 2-position followed by a Wittig reaction to generate the acrylate moiety.

Synthesis of functionalized pyrroloindolines: Via a visible-light-induced radical cascade reaction: Rapid synthesis of (±)-flustraminol B

The development of visible-light-induced synthesis of functionalized pyrroloindolines via a radical cascade reaction is reported. The reaction shows a broad substrate scope and highlights the mild nature of the reaction conditions. A range of substitutions on indole aromatic rings and N-centers is well tolerated, including a free allylic alcohol. Relying on the strategy, a rapid synthesis of (±)-flustraminol B was achieved.

Cation Triggered Domino Aza-Piancatelli Rearrangement/Friedel-Crafts Alkylation of Indole-Tethered Furfuyl Alcohols to Access Cycloocta[ b]indole Core of Alkaloids

A domino approach to bridged cycloocta[b]indolone through a cascade of aza-Piancatelli rearrangement/Friedel-Crafts alkylation is developed. This transformation has been realized by reaction of an indole-tethered 2-furylcarbinol and substituted aniline in the presence of a Lewis acid to initiate aza-Piancatelli rearrangement followed by an in situ intramolecular Friedel-Crafts alkylation to access bridged tetracyclic frameworks in one pot.

Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

Agent for Preventing or Ameliorating Hearing Impairment

It is to provide an agent for preventing or improving hearing loss, which comprises a low molecular compound which can be produced relatively easily and inexpensively as an active ingredient. One or more compounds selected from the group consisting of compounds represented by the following formulas (I0), (II), and (III) and a pharmaceutically acceptable salt of the compounds when R3 is OH are used as an agent for preventing or improving hearing loss.

Synthesis and anticancer activity of novel bisindolylhydroxymaleimide derivatives with potent GSK-3 kinase inhibition

Synthesis and biological evaluation of a series of novel indole derivatives as anticancer agents is described. A bisindolylmaleimide template has been derived as a versatile pharmacophore with which to pursue chemical diversification. Starting from maleimide, the introduction of an oxygen to the headgroup (hydroxymaleimide) was initially investigated and the bioactivity assessed by screening of kinase inhibitory activity, identifying substituent derived selectivity. Extension of the hydroxymaleimide template to incorporate substitution of the indole nitrogens was next completed and assessed again by kinase inhibition identifying unique selectivity patterns with respect to GSK-3 and CDK kinases. Subsequently, the anticancer activity of bisindolylmaleimides were assessed using the NCI-60 cell screen, disclosing the discovery of growth inhibitory profiles towards a number of cell lines, such as SNB-75 CNS cancer, A498 and UO-31 renal, MDA MB435 melanoma and a panel of leukemia cell lines. The potential for selective kinase inhibition by modulation of this template is evident and will inform future selective clinical candidates.

CHEMICAL SUBSTANCES WHICH INHIBIT THE ENZYMATIC ACTIVITY OF HUMAN KALLIKREIN-RELATED PEPTIDASE 6 (KLK6)

The invention relates to compounds which are suitable for the treatment of a disease associated with kallikrein-like peptidase 6 overexpression and to pharmaceutical compositions containing such compounds. The invention further relates to a kit of parts comprising such compounds or pharmaceutical compositions.