128942-88-1

Basic information

• Product Name: diethyl-4-1H-indole-2，3-dicarboxylate
• Synonyms: diethyl-4-1H-indole-2，3-dicarboxylate;Diethyl 1H-indole-2,3-dicarboxylate;2,3-diethyl ester1H-Indole-2,3-dicarboxylic acid;Diethyl-4-1H-indole-2,3-dicarboxylat
• CAS NO: 128942-88-1
• Molecular Formula: C14H15NO4
• Molecular Weight: 261.276
• Mol File: 128942-88-1.mol

Chemical Properties

• Melting Point: 128-129 °C
• Boiling Point: 390.789 °C at 760 mmHg
• Flash Point: 190.143 °C
• Appearance: /
• Density: 1.24 g/cm³
• Refractive Index: 1.593
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 13.43±0.30(Predicted)
• CAS DataBase Reference: diethyl-4-1H-indole-2，3-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl-4-1H-indole-2，3-dicarboxylate(128942-88-1)
• EPA Substance Registry System: diethyl-4-1H-indole-2，3-dicarboxylate(128942-88-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 128942-88-1(Hazardous Substances Data)

Usage

Uses

Used in Synthetic Chemistry:
Diethyl-4-1H-indole-2,3-dicarboxylate is used as a synthetic intermediate for the preparation of various complex organic molecules. Its carboxylate groups and indole ring structure provide unique reactivity that can be harnessed in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
Diethyl-4-1H-indole-2,3-dicarboxylate is used as a building block for the development of new drug candidates. Its unique structure and reactivity allow for the creation of novel compounds with potential therapeutic applications.
Used in Agrochemical Industry:
Diethyl-4-1H-indole-2,3-dicarboxylate is used as a key component in the synthesis of agrochemicals, such as pesticides and herbicides. Its functional groups can be tailored to create compounds with specific modes of action and improved efficacy.
Used in Specialty Chemicals:
Diethyl-4-1H-indole-2,3-dicarboxylate is used as a specialty chemical in various applications, such as in the production of dyes, pigments, and other materials that require its unique structural properties.
Note: The details of its safety and toxicity levels in human interaction are not widely available, so proper handling and precautions are highly recommended when dealing with this chemical.

InChI:InChI=1/C14H15NO4/c1-3-18-13(16)11-9-7-5-6-8-10(9)15-12(11)14(17)19-4-2/h5-8,15H,3-4H2,1-2H3

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Relevant articles and documents

Synthesis of 1h-indole-2,3-dicarboxylates via rhodium-catalyzed C-H annulation of arylhydrazines with maleates

This work describes a one-step synthesis of 1H-indole-2,3-dicarboxylates through C-H activation. Rhodiumcatalyzed tandem C-H activation and annulation of 2-acetyl-1-phenylhydrazines with maleates proceeded smoothly in the presence of additive NaOAc and oxidant Ag2CO3 and produced the corresponding indole derivatives, 1H-indole-2,3-dicarboxylates, in satisfactory to good yields. A variety of useful functional groups were tolerated on the benzene ring including halogen atoms (F, Cl, Br, and I) and methoxycarbonyl groups.

Photochemistry of ortho -Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent Control

The light-promoted potential of ortho -azidocinnamoyl compounds is evaluated for heterocycle synthesis. Depending on the nature of the solvent, 2-acylated indoles were obtained under aprotic conditions, whereas the use of a protic medium led to 2-substituted quinolines. The synthetic significance of this metal-free method is that, by simply changing the solvent, the reaction outcome can be directed towards different key heterocyclic scaffolds.

Synthesis of benzofused 1,4-azaborinols via [4 + 2] annulation strategy and its application in indole synthesis

We disclose herein, the first general synthesis of benzofused 1,4-azaborinols via [4 + 2] annulation strategy. These compounds have been synthesised from 2-amino phenylboronic acids/boronates and alkynes in excellent yields. Additionally, we demonstrate their synthetic application by reporting the first transformation of benzofused 1,4-azaborinols into functionalized indoles.

Regioselective synthesis of indoles via reductive annulation of nitrosoaromatics with alkynes

(equation presented) Indoles are produced regioselectively and in moderate yields by two new processes: (a) from the [Cp*Ru(CO)2]2-catalyzed reaction of nitrosoaromatics (ArNO) with alkynes under carbon monoxide and (b) in a two-step sequence involving the (uncatalyzed) reaction of ArNO with alkynes, followed by reduction of the intermediate adduct.

Regiospecific functionalization of indole-2-carboxylates and diastereoselective preparation of the corresponding indolines

The N-acyl derivatives of 3-substituted indole-2-carboxylates prepared through several routes were submitted to catalytic hydrogenation affording either cis- or trans-indoline diastereomers after quantitative C-2 epimerization.

Condensed Heteroaromatic Ring Systems; XVII: Palladium-Catalyzed Cyclization of β-(2-Halophenyl)amino Substituted α,β-Unsaturated Ketones and Esters to 2,3-Disubstituted Indoles

Palladium-catalyzed cyclization of β-(2-halophenyl)amino substituted α,β-unsaturated ketones and esters, prepared from 2-haloanilines by three different methods, gave 2,3-disubstituted indoles.