17017-71-9

Basic information

• Product Name: 1-benzyl-1H-indole-2-carboxylic acid
• Synonyms: 1-benzyl-1H-indole-2-carboxylic acid;1-(benzyl)indole-2-carboxylic acid;1-(phenylmethyl)-2-indolecarboxylic acid;1-(phenylmethyl)indole-2-carboxylic acid
• CAS NO: 17017-71-9
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.27992
• Mol File: 17017-71-9.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 496.3°C at 760 mmHg
• Flash Point: 254°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 1.14E-10mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-benzyl-1H-indole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-1H-indole-2-carboxylic acid(17017-71-9)
• EPA Substance Registry System: 1-benzyl-1H-indole-2-carboxylic acid(17017-71-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 17017-71-9(Hazardous Substances Data)

Usage

General Description

1-benzyl-1H-indole-2-carboxylic acid, also known as benzylindol-2-carboxylic acid, is a chemical compound with the molecular formula C19H15NO2. It is a derivative of indole and carboxylic acid, and it contains a benzyl group attached to the indole ring. 1-benzyl-1H-indole-2-carboxylic acid has potential applications in organic synthesis and medicinal chemistry due to its structural and functional properties. It may exhibit biological activities such as antimicrobial, antifungal, and anti-inflammatory effects, making it a promising candidate for drug development. Additionally, its aromatic and heterocyclic nature makes it useful in the production of dyes and pigments. Overall, 1-benzyl-1H-indole-2-carboxylic acid is a versatile chemical compound with various potential applications across different industries.

InChI:InChI=1/C16H13NO2/c18-16(19)15-10-13-8-4-5-9-14(13)17(15)11-12-6-2-1-3-7-12/h1-10H,11H2,(H,18,19)

Upstream product

• 121195-60-6 1-benzyl-indole-2,3-dicarboxylic acid 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 100-44-7 benzyl chloride 
• 81787-92-0 1-benzyl-1H-indole-2-carboxylic acid methyl ester 
• 3770-50-1 2-carbethoxyindole 
• 100-39-0 benzyl bromide 
• 1477-50-5 Indole-2-carboxylic acid 
• 2759-28-6 1-phenylmethylpiperazine 
• 1217-89-6 1-benzylisatin 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 17017-66-2 ethyl 1-benzyl-1H-indole-2-carboxylate 
• 124814-66-0 2-(Benzyl-phenyl-hydrazono)-propionic acid 
• 124814-66-0 2-(benzyl-phenyl-hydrazono)-propionic acid 

Downstream Products

• 17017-66-2 ethyl 1-benzyl-1H-indole-2-carboxylate 
• 17017-72-0 1-benzyl-1H-indole-2-carboxylic acid chloride 
• 668995-83-3 1-benzyl-1H-indole-2-carboxylic acid 2-piperidin-1-yl-ethyl ester 
• 348084-96-8 1-benzyl-1H-indole-2-carboselenoic acid Se-phenyl ester 
• 942157-40-6 perfluorophenyl 1-benzyl-1H-indole-2-carboxylate 

Relevant articles and documents

Calcium-Catalyzed Formal [5 + 2] Cycloadditions of Alkylidene β-Ketoesters with Olefins: Chemodivergent Synthesis of Highly Functionalized Cyclohepta[ b]indole Derivatives

The calcium-catalyzed, formal [5 + 2] cycloaddition of indolyl alkylidene β-ketoesters with mono- A nd disubstituted aryl olefins to form cyclohepta[b]indole derivatives has been established. Unanticipated chemodivergence with phenyl vinyl sulfide/ether revealed a double [5 + 2] cycloaddition cascade providing ethano-bridged cyclohepta[b]indoles. Overall, the method's highlights include: (1) use of a green, calcium-based catalyst (2.5 mol % loading); (2) reaction times under 1 h; (3) mild reaction conditions; (4) substrate-derived chemodivergence; (5) functional group tolerance; and (6) examples of derivatization.

Diversity oriented synthesis of β-carbolinone and indolo-pyrazinone analogues based on an Ugi four component reaction and subsequent cyclisation of the resulting indole intermediate

A one-pot domino multicomponent reaction for the rapid, integrated and versatile synthesis of highly functionalized β-carbolinones (9a-9ab) and indolo-pyrazinones (10a-10ab) has been established. The reaction involves an Ugi-four component reaction of ind

Synthesis of new functionalized indoles based on ethyl indol-2-carboxylate

Successful alkylations of the nitrogen of ethyl indol-2-carboxylate were carried out using aq. KOH in acetone. The respective N-alkylated acids could be obtained without separating the N-alkylated esters by increasing the amount of KOH and water. The use of NaOMe in methanol led to transesterification instead of the alkylation, while the use of NaOEt led to low yields of the N-alkylated acids. Hydrazinolysis of the ester gave indol-2-carbohydrazide which then was allowed to react with different aromatic aldehydes and ketones in ethanol catalyzed by acetic acid. Indol-2-thiosemicarbazide was used in a heterocyclization reaction to form thiazoles. The new structures were confirmed using NMR, mass spectrometry and X-ray single crystal analysis.