21139-32-2

Basic information

• Product Name: ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE
• Synonyms: AKOS JY2083663;ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE
• CAS NO: 21139-32-2
• Molecular Formula: C₁₇H₁₄ClNO₂
• Molecular Weight: 299.75
• Mol File: 21139-32-2.mol

Chemical Properties

• Melting Point: 176-178°C
• Boiling Point: 503.8 °C at 760 mmHg
• Flash Point: 258.5 °C
• Appearance: /
• Density: 1.283 g/cm³
• Vapor Pressure: 2.81E-10mmHg at 25°C
• Refractive Index: 1.642
• PKA: 13.84±0.30(Predicted)
• CAS DataBase Reference: ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE(21139-32-2)
• EPA Substance Registry System: ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE(21139-32-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 21139-32-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE is used as a reactant in carbonyl coupling reactions, which are essential for the formation of carbon-carbon bonds in organic chemistry. ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE serves as a key intermediate in the synthesis of complex organic molecules, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE is used as a building block for the development of novel drug candidates. Its unique chemical structure allows for the creation of diverse molecular entities with potential therapeutic applications, including the treatment of various diseases and disorders.
Used in Chemical Research:
ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE is also utilized in academic and industrial research settings for the investigation of new reaction pathways, catalysts, and synthetic methods. Its reactivity in carbonyl coupling reactions makes it an attractive candidate for studying the mechanisms and optimization of these processes, ultimately leading to more efficient and sustainable chemical synthesis techniques.
Used in Material Science:
In the field of material science, ETHYL 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYLATE can be employed as a component in the development of advanced materials with specific properties, such as optoelectronic devices, sensors, and other functional materials. Its incorporation into these systems can lead to improved performance and novel applications in various industries.

InChI:InChI=1/C17H14ClNO2/c1-2-21-17(20)16-15(11-6-4-3-5-7-11)13-10-12(18)8-9-14(13)19-16/h3-10,19H,2H2,1H3

Upstream product

• 620-79-1 Ethyl 2-benzylacetoacetate 
• 46115-41-7 phenyl pyruvic acid 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 4792-67-0 5-chloro-indole-2-carboxylic acid ethyl ester 
• 24139-99-9 ethyl 2-[2-(4-chlorophenyl)hydrazinylidene]-3-phenylpropanoate 
• 106-47-8 4-chloro-aniline 
• 17507-56-1 ethyl 2-diazo-2-(diethoxyphosphoryl)acetate 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 19144-20-8 N-(2-benzoyl-4-chlorophenyl)oxalamic acid ethyl ester 

Downstream Products

• 1032291-28-3 C₁₆H₁₁ClN₄S 

Relevant articles and documents

Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives

Abstract: A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR, su

Design, synthesis and pharmacophoric model building of new 3-alkoxymethyl/3-phenyl indole-2-carboxamides with potential antiproliferative activity

Novel 3-alkoxymethyl/3-phenyl indole-2-carboxamide derivatives were synthesized and evaluated for their anticancer activity. Most of the tested compounds showed moderate to excellent activity against the tested cell lines (MCF7 and HCT116). 3-Phenyl substitution on indole with p-piperidinyl phenethyl 24a and p-dimethylamino phenethyl 24c exhibited anticancer activity against MCF7 with IC50 of 0.13 and 0.14?μm, respectively. Further mechanistic study of the most active compounds through their action on cell cycle showed disturbance in cell cycle progression and cell cycle arrest. For future development of this series of compounds, pharmacophore study was conducted which indicated that the enhancement of the activity could be achieved through the addition of acceptor or donating groups to the already-present indole nucleus.

Structure-based virtual screening to get new scaffold inhibitors of the Ser/Thr protein kinase PknB from mycobacterium tuberculosis

In search of new inhibitors of the Ser/Thr protein kinase PknB from Mycobacterium tuberculosis we carried out a structure-based virtual screening study to identify ATP-competitive inhibitors of this enzyme. These studies point out that N-phenylmethylindole-2-carboxamide is a promising scaffold for the development of new PknB inhibitors. We synthesized a small set of analogue compounds to assess the pharmacophore structural requirements and to optimize the inhibitory activity against PknB. This strategy led to the identification of compound 3, endowed with an IC50 of 20 μM, which provides a novel scaffold for further improvement of PknB inhibitors.

Three-component Fischer indole synthesis

Three-component coupling between acyl chlorides, diazonium salts, and alcohols or amines allows the formation of-hydrazono carboxylic acid derivatives which may be directly converted into indoles by a Fischer-type cylization. Georg Thieme Verlag Stuttgart - New York.

Novel synthesis of 5-substituted-3-phenylindole-2-(1,2,4-triazole) derivatives

Various substituted 3-phenylindole 2-carboxylates (1a-c) were prepared according to the literature methods. These carboxylates (1a-c) on reaction with thiosemicarbazide yielded 5-substituted-3-phenylindol-2-(1,2,4-triazole-3- thione) (2a-c) on refluxing in pyridine for 8 h. The 5-substituted-3- phenylindole-2-[1,2,4-triazolo-3-thioacetic acid] (3a-c) were prepared from 5-substituted-3-phenyl indole-2-[1,2,4-triazole-3-thione] (2a-c) on reaction with an appropriate alkylating agent and sodium acetate in acetic acid. Further, (3a-c) were reacted with acetic anhydride to bring about a cyclocondensation reaction to yield 5-substituted-3-phenylindol-2-thiazolo(2,3-b)-triazole (4a-c). The 5-substituted-3-phenylindole-2-[1,2,4-triazolo-3-acetic acid] (3a-c) were reacted with o-phenylenediamino dihydrochloride in ethylene glycol to yield 5-substituted-3-phenylindole-1,2,4-triazolo-3′-yl-thiomethyl) benzimidazoles (5a-c). Copyright Taylor & Francis Group, LLC.

IDOLES USEFUL IN THE TREATMENT OF INFLAMMATION

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Construction of heterocyclic compounds by use of α-diazophosphonates: New one-pot syntheses of indoles and isocoumarins

(Matrix Presented) α-Diazophosphonates, which have extremely useful properties from a synthetic point of view, are disclosed as 1,1-ambiphilic one-carbon building blocks for one-pot construction of various heterocyclic compounds. They are easily prepared and have higher stability by the effect of the phosphoryl group than corresponding α-diazocarbonyl compounds. Using this synthon, we have developed a novel, mild, and efficient synthetic method of 2,3-disubstituted indoles and 3,4-disubstituted isocoumarins.

Carbonyl coupling reactions catalytic in titanium and the use of commercial titanium powder for organic synthesis

The high thermodynamic stability of titanium oxides formed as the inorganic byproducts in McMurry-type reactions has so far prevented the development of a catalytic procedure for such reductive carbonyl coupling processes. Similarly, a tightly bound oxide layer passivates the surface of commercial titanium, which is unreactive toward organic substrates under conventional conditions. This paper outlines a way to overcome both of these problems. Thus, oxoamides 1a-h can be reductively cyclized to indoles 2a-h using only catalytic amounts of low-valent titanium if the reaction is carried out in the presence of a chlorosilane. Specifically, the method is based upon the in situ generation of an activated titanium species from TiCl3 and Zn in the presence of the substrate, followed by regeneration of titanium chloride from the titanium oxides formed via ligand exchange with the admixed chlorosilane. Its proper choice is crucial for obtaining both good turnover numbers and clean conversions. Depending on the product structure, (TMS)Cl, ClMe2SiCH2CH2SiMe2Cl (5), or ClMe2Si(CH2)3CN (6) was found to be best suited. Similarly, chlorosilanes also effect the activation of commercial titanium powder which may then be used as a performant off-the-shelf reagent for various types of carbonyl and acetal coupling reactions, for the deoxygenation of epoxides and for the reductive cyclization of oxoamides or oxoesters to indoles, benzofurans, and 2-quinolones. Under these conditions retinal can be reductively dimerized to β-carotene in good yield. Moreover, the titanium/ chlorosilane reagent combination exhibits a strong template effect, allowing macrocyclization reactions without recourse to high dilution. Up to 36-membered rings have been closed in that way. 29Si NMR studies provide some insight into the elementary steps responsible for the degradation of the surface oxide layer on titanium by the chlorosilane. The effect of Lewis acid additives on the course of the coupling processes is discussed.

'High-surface sodium' as a reducing agent for TiCl 3

Sodium deposited on inorganic supports such as Al2O3, TiO2 and NaCl ('high-surface sodium') is a cheap, readily prepared, nonpyrophoric reducing agent for TiCl3. The low-valent titanium thus obtained, after only 1 h reduction time, is well suited for McMurry coupling reactions, particularly of aromatic carbonyl compounds. It exhibits a previously unrivalled template effect for the cyclization of dicarbonyl compounds to (macrocyclic) cycloalkenes and is suitable for the reduction of N-acyl-2-aminobenzophenone derivatives to 2,3-disubstituted indoles. Even a 36-membered ring could be formed without recourse to high dilution techniques.