141410-06-2

Basic information

• Product Name: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2S)-(9CI)
• Synonyms: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2S)-(9CI);Methyl (S)-Indoline-2-carboxylic acid;(S)-2,3-dihydro-1H-indol-2-carboxylic acid methyl ester;(S)-(+)-Methyl indoline-2-carboxylate;(S)-(+)-Methyl indoline-2-carboxylate >=97.0% (HPLC)
• CAS NO: 141410-06-2
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Product Categories: PYRROLE
• Mol File: 141410-06-2.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 292.8±19.0 °C(Predicted)
• Appearance: /
• Density: 1.164±0.06 g/cm3(Predicted)
• PKA: 3.11±0.40(Predicted)
• BRN: 5334940
• CAS DataBase Reference: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2S)-(9CI)(141410-06-2)
• EPA Substance Registry System: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2S)-(9CI)(141410-06-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 141410-06-2(Hazardous Substances Data)

Usage

General Description

1H-Indole-2-carboxylic acid, 2,3-dihydro-, methyl ester, (2S)-(9CI) is a chemical compound that belongs to the class of indole derivatives. It is a methyl ester of 1H-indole-2-carboxylic acid, and its molecular structure includes a 2,3-dihydro-indole ring with a carboxylic acid group and a methyl ester functional group. 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2S)-(9CI) is chiral, with the (2S) configuration indicating that the methyl ester group is on the second carbon of the indole ring. It may be used in various chemical and pharmaceutical applications, such as in the synthesis of pharmaceutical drugs or as an intermediate in organic synthesis. Due to its potential biological activity and structural features, it may also be of interest in research and development pursuits.

Upstream product

• 96056-64-3 (S)-indoline 2-carboxylic acid methyl ester hydrochloride 
• 197460-36-9 methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate 
• 109-21-7 butyl butyrate 
• 59040-84-5 indoline-2-carboxylic acid methyl ester 
• 938069-18-2 2-bromo-L-phenylalanine methyl ester 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 67-56-1 methanol 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 1477-50-5 Indole-2-carboxylic acid 
• 3770-50-1 2-carbethoxyindole 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 721968-93-0 3-methoxyphenyl allyl carbonate 
• 15022-08-9 diallylcarbonate 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 27640-31-9 2,3-Dihydro-1H-indol-2-ylmethanol 
• 108906-13-4 (R,S)-indoline-2-carboxylic acid amide 
• 313235-19-7 (S)-methyl 1-benzylindoline-2-carboxylate 
• 186704-03-0 methyl (+/-)-1-t-butoxycarbonyl-indoline-2-carboxylate 
• 160726-12-5 (S)-1-(4-Benzyloxycarbonylmethyl-2-methyl-oxazol-5-yl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester 
• 160726-11-4 (S)-1-((S)-2-Acetylamino-3-benzyloxycarbonyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester 
• 110659-07-9 N-acetyl-indoline-2-carboxylic acid methyl ester 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 293737-30-1 (R)-indoline-2-carboxylic acid methyl ester 
• 1061617-43-3 methyl (S)-N-(allyloxycarbonyl)indoline-2-carboxylate 
• 104672-02-8 (S)-butyl indoline-2-carboxylate 
• 1256479-04-5 (R)-butyl indoline-2-carboxylate 
• 135829-04-8 benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate 
• 135829-03-7 methyl (+/-)-1-benzyloxycarbonyl-indoline-2-carboxylate 

Relevant articles and documents

A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives

A thorough experimental and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Methyl (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.

Asymmetric Counteranion Directed Catalytic Heck/Tsuji-Trost Annulation of Aryl Iodides and 1,3-Dienes

A chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction of aryl iodides and 1,3-dienes is presented. Chiral indoline derivatives could be afforded with remarkably higher yields and enantioselectivities than our previous chiral ligand-based method. Silver carbonate is employed as both base and halide scavenger to ensure fast and recyclable exchange of the catalytic amount of chiral anions. Fast salt metathesis, as well as the acceleration effect of the chiral anion, could both benefit the stereocontrol of the reaction.

Enantioselective Reformatsky Reaction of Ketones Catalyzed by Chiral Indolinylmethanol

A reliable and practical Reformatsky reaction of ethyl iodide acetate with ketones for the synthesis of chiral β-hydroxyl carbonyl compounds in good yields and excellent enantioselectivities is presented. A readily available dihydroindole derivative was u