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

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

Uses

Used in Pharmaceutical Synthesis:
1H-Indole-2-carboxylic acid, 2,3-dihydro-, methyl ester, (2S)-(9CI) is utilized as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique molecular structure and chirality make it a valuable component in the development of new medications with specific therapeutic targets.
Used in Organic Synthesis:
In the field of organic synthesis, 1H-Indole-2-carboxylic acid, 2,3-dihydro-, methyl ester, (2S)-(9CI) serves as a building block for the creation of more complex organic molecules. Its reactivity and structural features facilitate its incorporation into a wide range of chemical products, contributing to the advancement of material science and specialty chemicals.
Used in Research and Development:
Due to its potential biological activity and distinctive structural attributes, 1H-Indole-2-carboxylic acid, 2,3-dihydro-, methyl ester, (2S)-(9CI) is of interest in research and development endeavors. It may be employed in studies aimed at understanding its interactions with biological systems, leading to the discovery of novel applications in medicine and other fields.

Upstream product

• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 67-56-1 methanol 
• 3770-50-1 2-carbethoxyindole 
• 1477-50-5 Indole-2-carboxylic acid 
• 96056-64-3 (S)-indoline 2-carboxylic acid methyl ester hydrochloride 
• 197460-36-9 methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate 
• 59040-84-5 indoline-2-carboxylic acid methyl ester 
• 15022-08-9 diallylcarbonate 
• 721968-93-0 3-methoxyphenyl allyl carbonate 
• 109-21-7 butyl butyrate 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 104-55-2 3-phenyl-propenal 
• 938069-18-2 2-bromo-L-phenylalanine methyl ester 
• 1440515-36-5 C₁₅H₁₄N₂O₄S 

Downstream Products

• 130659-48-2 C₂₅H₂₄N₂O₅ 
• 130659-48-2 C₂₅H₂₄N₂O₅ 
• 110659-07-9 N-acetyl-indoline-2-carboxylic acid methyl ester 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 293737-30-1 (R)-indoline-2-carboxylic acid methyl ester 
• 167633-66-1 1-phenylacetyl-2,3-dihydro-1H-indole-2-carboxylic acid 
• 27640-31-9 2,3-Dihydro-1H-indol-2-ylmethanol 
• 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 
• 1351469-47-0 methyl 1-(4-nitrophenyl)indoline-2-carboxylate 
• 135829-04-8 benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate 
• 135829-03-7 methyl (+/-)-1-benzyloxycarbonyl-indoline-2-carboxylate 
• 1202-04-6 indole-2-carboxylic acid methyl ester 

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.

Promoting the Furan Ring-Opening Reaction to Access New Donor–Acceptor Stenhouse Adducts with Hexafluoroisopropanol

Donor–acceptor Stenhouse adducts (DASAs) are visible-light-responsive photoswitches with a variety of emerging applications in photoresponsive materials. Their two-step modular synthesis, centered on the nucleophilic ring opening of an activated furan, ma

Chiral Arylated Amines via C?N Coupling of Chiral Amines with Aryl Bromides Promoted by Light

The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis. Over the past two decades or so, many improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays. However, there lacks a protocol that could be used to couple a wide range of chiral amines and aryl halides, without erosion of the enantiomeric excess (ee). Reported in this article is a method based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters. Its viability is demonstrated by 92 examples with up to 99 % ee.

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

Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines

Herein, we introduce one of the first examples of asymmetric organocatalyzed synthesis of 1,2-dihydropyridines, affording enantioselective access to and partially solving regioselectivity challenges in the synthesis of dihydropyridines. We demonstrate that through modification of organocatalysts both 1,2- and 1,4-dihydropyridines (1,2- and 1,4-DHPs) can be obtained with high regioselectivity (ratio of 1,2-DHP/1,4-DHP from 95/5 to 0/100) and enantioselectivity (33% ee for 1,2-DHPs and up to 98% ee for 1,4-DHPs) in good yields (up to 87%).

N-ALKYLSULFONYL INDOLINE COMPOUND, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE

In crop production in the fields of agriculture, horticulture and the like, the damage caused by insect pests etc. is still immense, and insect pests resistant to existing insecticides have emerged. Under such circumstances, the development of novel agricultural and horticultural insecticides is desired. The present invention provides an agricultural and horticultural insecticide comprising the indoline compound represented by the general formula (1): (wherein R1 and R4 are hydrogen atoms, R2 and R3 are halogen atoms, R5 is a haloalkyl group, Ra, Rb and Rc are hydrogen atoms, A1 is a CH group, A2 is a nitrogen atom, A3 is N-Me, m is 2, and n is 1), or a salt thereof as an active ingredient; and a method for using the insecticide.

Base-assisted intramolecular c-n coupling reaction from nh2-bound cyclopalladated l -phenylalanine to indoline-2-carboxylic acid

The deprotonative intramolecular-amination reaction of phenylalanine-derived palladacycles has been investigated to highlight a facile carbonate-assisted N-H activation before the C-N bond formation. A major counterion effect led to divergent pathways whereby the SPhos-Pd complexes with iodine, triflate, or trifluoroacetate anions were key intermediates to afford access to (S)-2-indolinecarboxylic acid derivatives.

GRANZYME B DIRECTED IMAGING AND THERAPY

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

Design and synthesis of novel indoline-(thio)urea hybrids

A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.