(5-Phenyl-1H-indol-3-yl)acetic acid

Base Information

• Chemical Name: (5-Phenyl-1H-indol-3-yl)acetic acid
• CAS No.: 168649-23-8
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.28000
• ChEMBL ID: CHEMBL419847
• DSSTox Substance ID: DTXSID80570014
• Nikkaji Number: J1.793.558E
• Wikidata: Q82457302
• Mol file: 168649-23-8.mol

Synonyms:5-Ph-IAA;168649-23-8;2-(5-phenyl-1H-indol-3-yl)acetic acid;(5-Phenyl-1H-indol-3-yl)acetic acid;1H-Indole-3-acetic acid, 5-phenyl-;5-Phenyl-1H-indole-3-acetic acid;starbld0014027;5-phenyl-indole-3-acetic acid;CHEMBL419847;SCHEMBL23701757;DTXSID80570014;GLXC-25859;EX-A6742;AKOS022555695;AT34792;MS-23552;PD158918;HY-134653;CS-0146825

Chemical Property of (5-Phenyl-1H-indol-3-yl)acetic acid

Chemical Property:

• Boiling Point: 521.3±35.0 °C(Predicted)
• PSA: 53.09000
• Density: 1.291±0.06 g/cm3(Predicted)
• LogP: 3.46200
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 251.094628657
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=C(C=C2)NC=C3CC(=O)O

Technology Process of (5-Phenyl-1H-indol-3-yl)acetic acid

There total 4 articles about (5-Phenyl-1H-indol-3-yl)acetic acid 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: 79.0%

phenyltin trichloride (1124-19-2) + (5-bromo-1H-indol-3-yl)-acetic acid (40432-84-6) → 5-(2-phenyl)-indole-3-acetic acid (168649-23-8)

Guidance literature:

With potassium hydroxide; disodium P-phenyl-3,3'-phosphinediyl-bis(benzenesulfonate); palladium dichloride; at 90 ℃; for 3h;

DOI:10.1016/0040-4039(95)00485-U

Reference yield:

2-(5-phenyl-1H-indol-3-yl)-2-oxoacetic acid → 5-(2-phenyl)-indole-3-acetic acid (168649-23-8)

Guidance literature:

With sodium methylate; hydrazine hydrate; In 2-ethoxy-ethanol; at 150 ℃; for 10h;

Reference yield:

5-phenyl-1H-indole (66616-72-6) → 5-(2-phenyl)-indole-3-acetic acid (168649-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBuLi / tetrahydrofuran / 0 °C

1.2: ZnCl₂

2.1: aq. NaOH / methanol

With sodium hydroxide; n-butyllithium; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(02)00505-X

upstream raw materials:

phenyltin trichloride

(5-bromo-1H-indol-3-yl)-acetic acid

5-phenyl-1H-indole