2-(1H-Indol-6-yl)acetic acid

Base Information

• Chemical Name: 2-(1H-Indol-6-yl)acetic acid
• CAS No.: 39689-58-2
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 2933998090
• European Community (EC) Number: 870-753-5
• DSSTox Substance ID: DTXSID40564979
• Wikidata: Q72482911
• Mol file: 39689-58-2.mol

Synonyms:2-(1H-Indol-6-yl)acetic acid;39689-58-2;1H-Indole-6-acetic acid;MFCD09837606;indol-6-acetic acid;indole-6-acetic acid;2-(indol-6-yl)acetic acid;(1H-Indol-6-yl)acetic acid;(1H-indol-6-yl)-acetic acid;SCHEMBL3105331;2-(1H-Indol-6-yl)aceticacid;AMY7551;DTXSID40564979;SWFCZJVRWYZLPW-UHFFFAOYSA-N;RB3238;AKOS004122026;CS-W021376;FS-3664;SB14723;SY047357;EN300-746249;A873592

Chemical Property of 2-(1H-Indol-6-yl)acetic acid

Chemical Property:

• Boiling Point: 415.03 °C at 760 mmHg
• PKA: 4.43±0.30(Predicted)
• Flash Point: 204.803 °C
• PSA: 53.09000
• Density: 1.355 g/cm³
• LogP: 1.79500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

99%, ^*data from raw suppliers

2-(1H-Indol-6-yl)aceticacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC2=C1C=CN2)CC(=O)O
• Use Description: 1H-Indole-6-acetic acid (9CI) is a chemical compound with various applications in different fields. In agriculture, it plays a crucial role as a plant growth regulator and auxin, which are compounds that influence plant growth and development. It is used to stimulate root formation, enhance fruit development, and control fruit drop in various crops, contributing to improved crop yields and quality. Additionally, in the pharmaceutical industry, 1H-Indole-6-acetic acid serves as a key starting material for the synthesis of pharmaceuticals and drug intermediates. Its role in drug development is significant, as it can lead to the creation of novel drugs and therapies for various medical conditions. Furthermore, in chemical research, it is used as a building block for the synthesis of diverse organic compounds, making it a valuable tool for understanding chemical reactions and developing new materials. Its multifaceted role in agriculture, pharmaceuticals, and chemical research underscores its importance in advancing these fields and scientific knowledge as a whole.

Technology Process of 2-(1H-Indol-6-yl)acetic acid

There total 9 articles about 2-(1H-Indol-6-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: 90.0%

2-(1-tosyl-1H-indole-6-yl)acetonitrile → 2-(indol-6-yl)acetic acid (39689-58-2)

Guidance literature:

With sodium hydroxide; In methanol; ethanol; dichloromethane;

Reference yield: 69.0%

2-(1H-indol-6-yl)acetonitrile (39689-57-1) → 2-(indol-6-yl)acetic acid (39689-58-2)

Guidance literature:

With lithium hydroxide; In water; isopropyl alcohol; at 75 ℃; for 25h;

Reference yield:

indole-6-carboxylic acid methyl ester (50820-65-0) → 2-(indol-6-yl)acetic acid (39689-58-2)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / 16 h / 80 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C

3: triethylamine; methanesulfonyl chloride / chloroform / 27 h / 20 °C

4: dimethyl sulfoxide / 48 h / 20 °C

5: water; sodium hydroxide / ethanol / 6 h / Reflux

With lithium aluminium tetrahydride; water; potassium carbonate; methanesulfonyl chloride; triethylamine; sodium hydroxide; In tetrahydrofuran; ethanol; chloroform; dimethyl sulfoxide;

upstream raw materials:

indole-6-carboxylic acid methyl ester

1-(tert-butoxycarbonyl)-1H-indole-6-carboxaldehyde

2-(1H-indol-6-yl)acetonitrile

indole-6-carboxaldehyde

Downstream raw materials:

2-(1H-indol-6-yl)-N-prop-2-ynyl-acetamide

methyl 2-(1H-indole-6-yl)acetate

Refernces

• 1、 -. "RING-FUSED COMPOUND". Paragraph 0330-0331. . Retrieved 2014/01/07.