3-(1H-indol-2-yl)aniline

Base Information

• Chemical Name: 3-(1H-indol-2-yl)aniline
• CAS No.: 6318-72-5
• Molecular Formula: C14H12 N2
• Molecular Weight: 208.263
• Hs Code.: 2933990090
• NSC Number: 31687
• DSSTox Substance ID: DTXSID90283466
• Nikkaji Number: J2.093.065I
• Wikidata: Q82018041
• ChEMBL ID: CHEMBL4213427
• Mol file: 6318-72-5.mol

Synonyms:3-(1H-indol-2-yl)aniline;6318-72-5;2-(3-Aminophenyl)-1H-indole;3-(1H-INDOL-2-YL)-PHENYLAMINE;MFCD00454976;NSC31687;3-(1H-Indole-2-yl)aniline;CHEMBL4213427;SCHEMBL11724742;DTXSID90283466;NSC 31687;NSC-31687;STK368625;AKOS000216113;BS-38260;F8889-3023

Chemical Property of 3-(1H-indol-2-yl)aniline

Chemical Property:

• Vapor Pressure: 2.99E-09mmHg at 25°C
• Boiling Point: 476.7°C at 760 mmHg
• Flash Point: 273.6°C
• PSA: 41.81000
• Density: 1.229g/cm³
• LogP: 3.99830
• Sensitive.: Light Sensitive
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 208.100048391
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-(1H-Indol-2-yl)aniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)C3=CC(=CC=C3)N
• Uses: 3-(1H-Indol-2-yl)aniline is an intermediate; used in preparation of acylguanidines as inhibitors of Hedgehog protein signalling pathway for treatment of cancer, neurodegenerative diseases and diabetes.

Technology Process of 3-(1H-indol-2-yl)aniline

There total 5 articles about 3-(1H-indol-2-yl)aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1-(3-aminophenyl)ethanone (99-03-6) + phenylhydrazine (100-63-0) → 2-(3'-amino-phenyl)-indole (6318-72-5)

Guidance literature:

1-(3-aminophenyl)ethanone; phenylhydrazine;

With polyphosphoric acid;

DOI:10.1002/ardp.201700299

Reference yield: 86.0%

2-(3-nitrophenyl)-1H-indole (6127-50-0) → 2-(3'-amino-phenyl)-indole (6318-72-5)

Guidance literature:

With tin(II) chloride hydrate; In ethanol; at 80 ℃; for 2h;

Reference yield: 60.0%

2-iodophenylamine (615-43-0) + 3-acetylenephenylamine (54060-30-9) → 2-(3'-amino-phenyl)-indole (6318-72-5)

Guidance literature:

2-iodophenylamine; 3-acetylenephenylamine; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; In N,N-dimethyl acetamide; at 20 ℃; for 1h;

With sodium hydroxide; In N,N-dimethyl acetamide; at 140 ℃;

DOI:10.1039/c2ob26456k

upstream raw materials:

1-(3-aminophenyl)ethanone

2-(3-nitrophenyl)-1H-indole

2-iodophenylamine

3-acetylenephenylamine

Downstream raw materials:

N-(3-(1H-indol-2-yl)phenylcarbamothioyl)-3,4,5-trimethoxybenzamide

N-(N-(3-(1H-indol-2-yl)phenyl)carbamimidoyl)-3,4,5-trimethoxybenzamide

Refernces

• 1、 Prior, Allan M.,Yu, Xufen,Park, Eun-Jung,Kondratyuk, Tamara P.,Lin, Yan,Pezzuto, John M.,Sun, Dianqing. "Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1". . p. 5393 - 5399. Retrieved 2017/11/20.
• 2、 Solinas, Antonio,Faure, Hélène,Roudaut, Hermine,Traiffort, Elisabeth,Schoenfelder, Angèle,Mann, André,Manetti, Fabrizio,Taddei, Maurizio,Ruat, Martial. "Acylthiourea, acylurea, and acylguanidine derivatives with potent Hedgehog inhibiting activity". supporting information; experimental part. p. 1559 - 1571. Retrieved 2012/04/17.