50614-84-1

Basic information

• Product Name: Ethyl 1H-indole-4-carboxylate
• Synonyms: Ethyl 1H-indole-4-carboxylate;Ethyl indole-4-carboxylate
• CAS NO: 50614-84-1
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Product Categories: blocks;Carboxes;IndolesOxindoles
• Mol File: 50614-84-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 70-71 °C
• Boiling Point: 342.4 °C at 760 mmHg
• Flash Point: 160.9 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 7.57E-05mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.83±0.30(Predicted)
• CAS DataBase Reference: Ethyl 1H-indole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 1H-indole-4-carboxylate(50614-84-1)
• EPA Substance Registry System: Ethyl 1H-indole-4-carboxylate(50614-84-1)

Safety Data

• Hazardous Substances Data: 50614-84-1(Hazardous Substances Data)

Usage

General Description

Ethyl 1H-indole-4-carboxylate is a chemical compound with the molecular formula C12H11NO2. This substance belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. It's often utilized as an intermediate for the synthesis of various pharmaceuticals and other complex organic compounds. Its structure consists of an ethyl group attached to an indole ring, which is a fused double ring system, with a carboxylate group at the 4th position. The compound is less commonly known, but it is an important tool in medicinal chemistry and drug discovery. Its CAS registry number is 16759-30-7.

InChI:InChI=1/C11H11NO2/c1-2-14-11(13)9-4-3-5-10-8(9)6-7-12-10/h3-7,12H,2H2,1H3

Upstream product

• 2124-55-2 1H-indole-4-carboxylic acid 
• 64-17-5 ethanol 
• 91873-13-1 3-ethoxy-5-nitro-3,4-dihydroisocoumarin 
• 52488-36-5 4-bromo-1H-indole 
• 201230-82-2 carbon monoxide 
• 7664-93-9 sulfuric acid 
• 91873-14-2 5-amino-3-ethoxy-3,4-dihydroisocoumarin 
• 112447-71-9 4-ethoxycarbonyl-1-tri-isopropylsilylindole 
• 141-52-6 sodium ethanolate 
• 71516-34-2 2-((E)-2-Dimethylamino-vinyl)-3-nitro-benzoic acid ethyl ester 
• 59382-60-4 ethyl 2-methyl-3-nitrobenzoate 
• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 120-72-9 indole 
• 31706-23-7 ethyl 2-bromo-3-nitrobenzoate 

Downstream Products

• 1074-85-7 (1H-indol-4-yl)methanol 
• 1093258-02-6 ethyl 1-methyl-1H-indole-4-carboxylate 
• 862297-60-7 4-[(tert-butyldiphenylsilyloxy)methyl]indole 
• 862297-61-8 4-[(tert-butyldiphenylsilyloxy)methyl]indole-3-carboxaldehyde 
• 862297-62-9 ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate 
• 862297-63-0 ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate 
• 862297-56-1 4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indole-3-carboxaldehyde 
• 98664-90-5 ethyl (6aRS,9SR,9aSR)-hexahydro-7,7-dimethylisoindolo[4,5,6-cd]indole-9-carboxylate 
• 1381993-11-8 1-(5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester 
• 1381992-68-2 (S,S,S)-N,N'-(3,3'-(ethane-1,2-diylbis(oxy))bis(propane-3,1-diyl))bis(1-(5-((S)-1-((S)-3-methyl-2-((S)-2-(methylamino)-propanamido)butanoyl)pyrrolidin-2-yl)pyridin-3-yl)-1H-indole-4-carboxamide) 
• 1074-86-8 4-formyl indole 
• 90924-06-4 1-methyl-1H-indole-4-carboxylic acid 
• 887922-92-1 indole-4-isocyanate 

Relevant articles and documents

HTS-based discovery and optimization of novel positive allosteric modulators of the α7 nicotinic acetylcholine receptor

HTS campaign of the corporate compound collection resulted in a novel, oxalic acid diamide scaffold of α7 nACh receptor positive allosteric modulators. During the hit expansion, several derivatives, such as 4, 11, 17 demonstrated not only high in vitro potency, but also in vivo efficacy in the mouse place recognition test. The advanced hit molecule 11 was further optimized by the elimination of the putatively mutagenic aromatic-amine building block that resulted in a novel, aminomethylindole compound family. The most balanced physico-chemical and pharmacological profile was found in case of compound 55. Docking study revealed an intersubunit binding site to be the most probable for our compounds. 55 demonstrated favorable cognitive enhancing profile not only in scopolamine-induced amnesia (place recognition test in mice) but also in natural forgetting (novel object recognition test in rats). Compound 55 was, furthermore, active in a cognitive paradigm of high translational value, namely in the rat touch screen visual discrimination test. Therefore, 55 was selected as a lead compound for further optimization. Based on the obtained favorable results, the invented aminomethylindole cluster may provide a viable approach for cognitive enhancement through positive allosteric modulation of α7 nAChRs.

An efficient procedure for the deprotection of N-pivaloylindoles, carbazoles and β-carbolines with LDA

Treatment of variously substituted indoles with 2 equivalents of LDA at 40-45 °C led to their fast and efficient deprotection. This method was also extended to N-pivaloylcarbazoles and β-carbolines.

The synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfones

The first synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfone precursors has been achieved. The required sulfones, 3,4,5,6- tetrahydro-1H-cyclohex[cd]benzothiophene-2,2-dioxide and 1,3,4,5,6,7- hexahydrocyclohept[cd]benzothiophene-2,2-dioxide, were prepared from α- tetralone and benzosuberone utilizing a ring closure proceeding through a sulfonium salt intermediate. The same strategy failed when frying to prepare the tricyclic sulfone of the indane series. Other contrasting reactivity was also noticed when comparing the ability and ease of formation of tricyclic ether compounds. These results indicate that the later ring system is considerably strained.