141452-01-9

Basic information

• Product Name: methyl indoline-5-carboxylate
• Synonyms: methyl indoline-5-carboxylate;Methyl 2,3-dihydro-1H-indole-5-carboxylate;2,3-Dihydro-1H-indol-5-carboxylic acid methyl ester
• CAS NO: 141452-01-9
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.19984
• Mol File: 141452-01-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: 67-69 °C
• Boiling Point: 330.955 °C at 760 mmHg
• Flash Point: 153.956 °C
• Appearance: /
• Density: 1.162 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Refrigerated.
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 2.65±0.20(Predicted)
• CAS DataBase Reference: methyl indoline-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl indoline-5-carboxylate(141452-01-9)
• EPA Substance Registry System: methyl indoline-5-carboxylate(141452-01-9)

Safety Data

• Hazardous Substances Data: 141452-01-9(Hazardous Substances Data)

Usage

General Description

Methyl indoline-5-carboxylate is an organic compound with the chemical formula C11H11NO2 and a molecular weight of 189.21 g/mol. It is a derivative of indoline, a bicyclic organic compound that contains a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Methyl indoline-5-carboxylate is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. It can also be used as a precursor for the preparation of various organic compounds through chemical reactions such as esterification or amidation. Additionally, methyl indoline-5-carboxylate has been studied for its potential biological activities, including as an antifungal and antimicrobial agent.

InChI:InChI=1/C10H11NO2/c1-13-10(12)8-2-3-9-7(6-8)4-5-11-9/h2-3,6,11H,4-5H2,1H3

Upstream product

• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 1011-65-0 5-methoxycarbonylindole 
• 153497-12-2 methyl 1-acetylindoline-5-carboxylate 
• 67-56-1 methanol 
• 15861-30-0 2,3-dihydro-1H-indole-5-formic acid 
• 7664-93-9 sulfuric acid 
• 153247-93-9 1-acetylindoline-5-carboxylic acid 

Downstream Products

• 712319-44-3 1-methanesulfonyl-2,3-dihydro-1H-indole-5-carboxylic acid 
• 1011-65-0 5-methoxycarbonylindole 
• 101460-85-9 1H-indole-5-carboxylic acid, 2,3-dihydro-2,3-dioxo-, methyl ester 

Relevant articles and documents

Rh(III)-Catalyzed C7-Thiolation and Selenation of Indolines

The rhodium(III)-catalyzed intermolecular C7-thiolation and selenation of indolines with disulfides and diselenides were developed. This protocol relies on the use of a removable pyrimidyl directing group to access valuable C-7 functionalized indoline scaffolds with ample substrate scope and broad functional group tolerance.

Pd/C-Catalyzed transfer hydrogenation ofN-H indoles with trifluoroethanol and tetrahydroxydiboron as the hydrogen source

Under the guidance of the known mechanism of the hydrogenation of indoles and transfer hydrogenation with tetrahydroxydiboron (B2(OH)4), Pd/C catalyzed transfer hydrogenation ofN-H indoles with trifluoroethanol and tetrahydroxydiborane as the hydrogen source has been developed. This provides an efficient strategy and catalytic system for the reduction of un-activatedN-H indoles, andN-H indolines are obtained with good to excellent yields. In addition, a series of the isotopic labelling experiments were carried out to probe the mechanism.

Heterogeneous catalytic hydrogenation of unprotected indoles in water: A green solution to a long-standing challenge

An environmentally benign procedure for the hydrogenation of unprotected indoles is described. The hydrogenation reaction is catalyzed by Pt/C and activated by p-toluenesulfonic acid in water as a solvent. The efficacy of the method is illustrated by the hydrogenation of a variety of substituted indoles to their corresponding indolines which were obtained in excellent yields.

Manganese(III) Acetate Catalyzed Aerobic Dehydrogenation of Tertiary Indolines, Tetrahydroquinolines and an N-Unsubstituted Indoline

A Mn(OAc)3 ? 2H2O-catalyzed aerobic dehydrogenation of five and six-membered N-heterocycles for the synthesis of N-heteroarenes is reported. Of note, this protocol can be applied to the dehydrogenation of tertiary indolines with various electron-deficient N-substituents. Preliminary mechanistic investigations support that a single-electron transfer pathway might be involved. (Figure presented.).

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.