32566-01-1

Basic information

• Product Name: 2-(2-AMINOPHENYL)INDOLE
• Synonyms: 2-(2'-AMINOPHENYL)INDOLE;2-(2-AMINOPHENYL)INDOLE;2-(2-Aminophenyl)indole 97%;2-(1H-indol-2-yl)-Benzenamine
• CAS NO: 32566-01-1
• Molecular Formula: C₁₄H₁₂N₂
• Molecular Weight: 208.26
• Product Categories: Intermediates of Dyes and Pigments;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 32566-01-1.mol

Chemical Properties

• Melting Point: 154-155 °C(lit.)
• Boiling Point: 437.9°Cat760mmHg
• Flash Point: 248.8°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 7.2E-08mmHg at 25°C
• Refractive Index: 1.726
• PKA: 16.53±0.30(Predicted)
• CAS DataBase Reference: 2-(2-AMINOPHENYL)INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-AMINOPHENYL)INDOLE(32566-01-1)
• EPA Substance Registry System: 2-(2-AMINOPHENYL)INDOLE(32566-01-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 32566-01-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Aminophenyl)indole is used as a reactant in cascade reactions of benzopyranylidenemalonates with monoand dinucleophiles for the synthesis of complex organic molecules with potential pharmaceutical applications.
Used in Antimicrobial Agents Production:
2-(2-Aminophenyl)indole is used as a reactant for the preparation of mono-, bis-indolo[1,2-c]quinazolines, which exhibit antimicrobial properties and can be used in the development of new antibiotics.
Used in Antimalarial Agents Production:
2-(2-Aminophenyl)indole is used as a reactant in the synthesis of isocryptolepine alkaloid, which possesses antimalarial activity and can be utilized in the development of new treatments for malaria.
Used in Antitumor Agents Production:
2-(2-Aminophenyl)indole is used as a reactant for the preparation of cyanoindolo[3,2-c]quinolines and benzimidazo[1,2-c]quinazolines, which have antitumor properties and can be employed in the development of new cancer therapies.
General Description:
2-(2-Aminophenyl)indole is an indole derivative with a wide range of applications in the synthesis of biologically active compounds. Its ability to undergo condensation reactions with various reagents makes it a valuable amination reagent in organic chemistry.

InChI:InChI=1/C14H12N2/c15-12-7-3-2-6-11(12)14-9-10-5-1-4-8-13(10)16-14/h1-9,16H,15H2

Upstream product

• 238398-39-5 2-(2-aminophenyl)-3-bromoindole 
• 107127-66-2 2-nitrobenzyl 2-nitrophenyl ketone 
• 131298-21-0 2-[(2-aminophenyl)ethynyl]phenylamine 
• 59050-53-2 2-(2-nitrophenyl)-1H-indole 
• 64-17-5 ethanol 
• 141-78-6 ethyl acetate 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 52670-38-9 2-ethynylaniline 
• 681462-57-7 2.2'-dinitro-tolan dibromide 
• 551-93-9 2-aminoacetophenone 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 201230-82-2 carbon monoxide 

Downstream Products

• 58995-87-2 N-[2-(1H-indol-2-yl)phenyl]benzamide 
• 159021-62-2 6-methylindolo<1,2-c>quinazoline 
• 4295-28-7 6-methyl-11H-indolo[3,2-c]-quinoline 
• 58995-86-1 N-[2-(1H-indol-2-yl)phenyl]acetamide 
• 110423-27-3 6-phenyl-indolo[1,2-c]quinazoline 
• 109813-74-3 2-(1-benzoyl-indol-2-yl)-aniline 
• 102311-55-7 toluene-4-sulfonic acid-(2-indol-2-yl-anilide) 
• 102704-20-1 phenyl-acetic acid-(2-indol-2-yl-anilide) 
• 112299-25-9 6-benzyl-indolo[1,2-c]quinazoline 
• 65610-86-8 2-(2-aminophenyl)-1-methyl-1H-indole 
• 88207-49-2 2-(2-aminophenyl)-3-chloro-1-phenylsulphonylindole 
• 125187-98-6 C₃₂H₂₅N₂P 
• 18735-98-3 5,11-dihydro-indolo[3,2-c]quinolin-6-one 
• 543745-48-8 [2-(1H-indol-2-yl)phenyl]-urea 

Relevant articles and documents

New indolo[1,2-c]quinazolines for single-crystal field-effect transistor: A united experimental and theoretical studies

Here, we account the synthesis and characterization of a series of symmetrical fused heterocyclic aromatic hydrocarbons (HAHs) with an indolo[1,2-c]quinazoline (IQ) as the core moiety. All the new HAHs IQ series were systematically investigated by using various spectroscopic methods. Furthermore, their photo-physical properties were supported by density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies to support the experimental findings. The tetramethyl-substituted indolo[1,2-c]quinazoline (TMIQ) compound is shown to exhibit the shifted type of π–π stacking interactions, which render this series as a new semiconducting material. Single-crystal-based field-effect transistor devices of TMIQ exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.25 cm2?V?1?s?1 with an on/off ratio of 5 × 105.

Selective C?H or N?H Imidoylative Annulation of 2-(2-Isocyanophenyl)-1H-indoles Leading to Diverse Indole-fused Scaffolds

2-(2-Isocyanophenyl)-1H-indoles, a class of functionalized isocyanides containing both aromatic C?H and indolo N?H functionalities, are first applied in selective imidoylative annulation reactions. Scaffolds of 6-aryl 11H-indolo[3,2-c]quinoline and 6-aryl

Selective CH or NH Imidoylative Annulation of 2-(2-Isocyanophenyl)-1H-indoles Leading to Diverse Indole-fused Scaffolds

2-(2-Isocyanophenyl)-1H-indoles, a class of functionalized isocyanides containing both aromatic CH and indolo NH functionalities, are first applied in selective imidoylative annulation reactions. Scaffolds of 6-aryl 11H-indolo[3,2-c]quinoline and 6-aryl i

TFAA-Catalyzed Annulation Synthesis of Spiro Pyrrolo[1,2-a]quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Benzoquinones/Ketones

A metal-free trifluorosulfonate anhydride (TFAA)-catalyzed strategy for the synthesis of spiro pyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and benzoquinones/ketones has been developed. With this general method, spiro pyrrolo[1,2-a]quinoxalin

Novel convenient one-pot method for the synthesis of indoloquinolines

A novel one-pot method based on the sequence of the Fisher reaction between nitroacetophenone and phenylhydrazines, the reduction with metallic tin directly in polyphosphoric acid, and acylation has been developed for the synthesis of indoloquinolines. Th

HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

The present invention relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting device comprising the same. According to the present invention, the heterocyclic compound represented by the chemical formula 1 may be

Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal

An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2-c]quinazolines is described. The Pd-catalyzed reaction of o-(oaminophenylethynyl) trifluoroacetanilides with Ar-B(OH)2 afforded 2-(o-aminophenyl)-3-arylindoles, that were converted to 1

A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities

A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C-C and C-N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.

Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives

An efficient, green, and novel method for the synthesis of N-heterocycle-fused quinoxalines is reported herein. Dimethyl sulfoxide was used as both a reactant and a solvent in this reaction. A wide range of products in moderate to excellent yields were obtained, including pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, 1H-pyrrolo[3,2-c]quinolines, and benzo[4,5]imidazo[1,2-c]quinazolines.

Tert -Butyl nitrite (TBN) as the N atom source for the synthesis of substituted cinnolines with 2-vinylanilines and a relevant mechanism was studied

A green method to synthesize cinnolines by 6π electrocyclic reaction with alkenyl amines and TBN has been developed. TBN plays a dual role both as a nitrogen atom source and an oxidant in this procedure. Relevant mechanism experiments reveal that the reaction proceeds through electrocyclic reaction and with diazo hydroxide as a key intermediate.