5-HYDROXYINDOLE-3-ACETIC ACID

Base Information

• Chemical Name: 5-HYDROXYINDOLE-3-ACETIC ACID
• CAS No.: 1321-73-9
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.186
• Mol file: 1321-73-9.mol

Synonyms:HYDROXYINDOLYL-3-ACETIC ACID, 5-;5-HYDROXYINDOLE-3-ACETIC ACID;5-HYDROXYINDOLYACETIC ACID;5-HYDROXYINDOLYL-3-ACETIC ACID;5-HIAA;5-HYDROXY-3-INDOLEACETIC ACID;(5-HYDROXY-1H-INDOL-3-YL)-ACETIC ACID;TIMTEC-BB SBB003639

Chemical Property of 5-HYDROXYINDOLE-3-ACETIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 161-164 °C (dec.)(lit.)
• Boiling Point: 497.054°C at 760 mmHg
• Flash Point: 254.409°C
• PSA: 73.32000
• Density: 1.497g/cm³
• LogP: 1.50060
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

5-Hydroxyindole-3-acetic acid ≥98% (HPLC), crystalline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (5-Hydroxy-1H-indol-3-yl)acetic acid is an intermediate in the preparation of magnolol derivatives with antidepressive potentials. A biochemical marker of neuroendocrine tumor. 5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.

Technology Process of 5-HYDROXYINDOLE-3-ACETIC ACID

There total 7 articles about 5-HYDROXYINDOLE-3-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:

2-(5-benzyloxy-1H-indol-3-yl)acetic acid (4382-53-0) → 5-Hydroxyindole-3-acetic acid (54-16-0,1321-73-9)

Guidance literature:

With palladium on activated charcoal; ethyl acetate;

DOI:10.1021/jo01084a008 DOI:10.1021/ja01651a001

Reference yield:

5-benzyloxygramine (1453-97-0) → 5-Hydroxyindole-3-acetic acid (54-16-0,1321-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaCN; aqueous ethanol

2: palladium/charcoal; ethanol

With palladium on activated charcoal; ethanol; sodium cyanide;

DOI:10.1021/jo01084a008 DOI:10.1021/ja01651a001

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) → 5-Hydroxyindole-3-acetic acid (54-16-0,1321-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; dioxane

2: NaCN; aqueous ethanol

3: palladium/charcoal; ethanol

With 1,4-dioxane; palladium on activated charcoal; ethanol; sodium cyanide; acetic acid;

DOI:10.1021/ja01651a001

upstream raw materials:

5-methoxy-1H-indole-3-acetic acid

2-(5-benzyloxy-1H-indol-3-yl)acetic acid

5-methoxyindole-3-acetonitrile

5-benzyloxy-1H-indole

Downstream raw materials:

(5-methoxy-1H-indol-3-yl)acetic acid methyl ester

2-(5-hydroxy-1H-indol-3-yl)-N-(1-(2-methyl-4-phenylthiazol-5-yl)-2-phenylethyl)acetamide

N-(2-(3,5-difluorophenyl)-1-(5-(o-tolyl)thiazol-4-yl)ethyl)-2-(5-hydroxy-1H-indol-3-yl)acetamide

2-(5-hydroxy-1H-indol-3-yl)-N-(2-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethyl)acetamide

Refernces

• 1、 ASERO,COLO,VERCELLONE. "Preparation of 5-hydroxy-indoleacetic acid.". . p. 219 - 220. Retrieved 2007/10/04.