53855-47-3

Basic information

• Product Name: ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE
• Synonyms: ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE;Ethyl 2-Methyl-3-indolecarboxylate;ethyl 2-Methyl-1H-indole-3-carboxylate;2-Methylindole-3-carboxylic acid ethyl ester;Ethyl 2-methylindole-3-carboxylate 99%
• CAS NO: 53855-47-3
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• Product Categories: pharmacetical;Indole;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles;alcohol|carboxylic ester
• Mol File: 53855-47-3.mol

Chemical Properties

• Melting Point: 134-136 °C(lit.)
• Boiling Point: 344.1 °C at 760 mmHg
• Flash Point: 161.9 °C
• Appearance: /
• Density: 1.177 g/cm³
• Vapor Pressure: 6.72E-05mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.99±0.30(Predicted)
• CAS DataBase Reference: ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE(53855-47-3)
• EPA Substance Registry System: ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE(53855-47-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 53855-47-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE is used as a reactant for the preparation of 2-methyl-3-[5-substituted phenyl-1,3,4-oxadiazol-2-yl]-1H-indoles, which are known for their antimicrobial properties. These compounds can be utilized in the development of new drugs to combat various microbial infections.
Used in Chemical Synthesis:
ETHYL 2-METHYL-2,3-DIHYDRO-INDOLE-3-CARBOXYLATE is used as a key intermediate in the synthesis of Aminoheterocycles via N-amination of heterocyclic compounds with O-benzoylhydroxylamines. This application is significant in the field of organic chemistry, as it allows for the creation of novel heterocyclic compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C12H13NO2/c1-3-15-12(14)11-8(2)13-10-7-5-4-6-9(10)11/h4-7,13H,3H2,1-2H3

Upstream product

• 77435-11-1 ethyl 1-benzyl-2-methyl-1H-indole-3-carboxylate 
• 6078-46-2 ethyl 3-(2-phenylhydrazono)butanoate 
• 128942-81-4 (Z)-ethyl 3-(2-iodophenylamino)-but-2-enoate 

Downstream Products

• 919119-66-7 ethyl 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-3-carboxylate 
• 1450659-45-6 ethyl 1-(1-(4-chlorophenyl)ethyl)-2-methyl-1H-indole-3-carboxylate 
• 1450657-89-2 ethyl 2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxylate 
• 1450652-71-7 C₂₆H₂₆ClN₃O₂ 
• 1450659-48-9 1-(1-(4-chlorophenyl)ethyl)-2-methyl-1H-indole-3-carboxylic acid 
• 1450651-94-1 N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxamide 
• 1450651-32-7 N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxamide 
• 1450657-91-6 2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxylic acid 
• 944335-36-8 ethyl 1-phenylsulfonyl-2-methylindole-3-carboxylate 
• 122946-81-0 3-propyl-4-(p-tolylsulfonyl)-<2H>-1,4-dihydropyrano<4,3-b>indole 
• 122946-82-1 3,3-dimethyl-4-(p-tolylsulfonyl)-<2H>-1,4-dihydropyrano<4,3-b>indole 
• 122946-83-2 4-<(benzyloxy)methyl>-3-propyl-<2H>-1,4-dihydropyrano<4,3-b>indole 
• 122946-84-3 4-<(benzyloxy)methyl>-3,3-dimethyl-<2H>-1,4-dihydropyrano<4,3-b>indole 
• 95-20-5 2-methyl-1H-indole 

Relevant articles and documents

Novel synthesis of fused indoles and 2-substituted indoles by the palladium-catalyzed cyclization of N-cycloalkenyl-o-haloanilines

A new palladium-catalyzed cyclization of N-alkenyl-o-haloanilines with selective isomerization of a double bond followed by formal 5-endo-trig cyclization was developed. A variety of fused and 2-substituted indoles were synthesized from enaminoesters prepared by condensation of β-ketoesters and o-iodoaniline.

Transformations of phenylhydrazones of dialkyl 2-oxo-propane-1,3- dicarboxylate and of ethyl acetoacetate in concentrated sulfuric acid

The hydrazones 3a,b, prepared from phenylhydrazine (1) and dialkyl 2-oxopropane-1,3-dicarboxylate (2a,b) were converted in concentrated sulfuric acid at -5 °C into a mixture of alkyl (3-carboxyindol-2-yl)acetates (5a,b), and ethyl (5-ethoxy-1-phenyl-1H-pyrazol-3-yl)acetate 6. The hydrazone 8, prepared from 1 and ethyl acetoacetate (7) was transformed under the same conditions into a mixture of five compounds: ethyl 2-methylindol-3-carboxylate (9), 2-methylindol-3-carboxylic acid (10), 2-methylindol (11), 5-ethoxy-3-methyl-1-phenyl-1H-pyrazole (12), and 3-methyl-1-phenyl-1H-pyrazol-5- one (13).

Fischer Indole Synthesis of 3-Acyl and 3-Alkoxy-carbonylindoles

N-Benzyl-N-phenylhydrazine derivatives of 1,3-diketones and 1,3-ketoesters undergo normal Fischer cyclisations to indoles, but no method could be found for the subsequent removal of the N-protecting group.No method could be found for the indolisation of N-aroyl-N-phenylhydrazine derivatives of dimedone with retention of the N-protecting group, though heating in tetralin did effect the electrocyclic step of the Fischer sequence and the formation of a carbon-carbon bond.