N-Acetylindoxyl

Base Information

• Chemical Name: N-Acetylindoxyl
• CAS No.: 33025-60-4
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 2933998090
• European Community (EC) Number: 608-822-7
• DSSTox Substance ID: DTXSID80186694
• Nikkaji Number: J2.368.985E
• Wikidata: Q27089400
• Metabolomics Workbench ID: 50050
• Mol file: 33025-60-4.mol

Synonyms:N-Acetyl-3-hydroxyindole;33025-60-4;N-Acetylindoxyl;1-(3-Hydroxy-1H-indol-1-yl)ethanone;1-ACETYL-3-HYDROXYINDOLE;1-(3-hydroxyindol-1-yl)ethanone;Acetylindoxyl;1H-Indol-3-ol, 1-acetyl-;1-acetyl-1H-indol-3-ol;1-(3-hydroxy-1H-indol-1-yl)ethan-1-one;C02298;1-acetyl-1H-indole-3-ol;1-ACETYLINDOL-3-OL;SCHEMBL1333179;1H -Indol-3-ol, 1-acetyl-;CHEBI:15363;DTXSID80186694;AMY18951;MFCD00047261;AKOS003630972;AB02040;4-Aminotetrahydro-2H-pyran hydrochloride;AS-49952;1-[(3-hydroxy-1H-indol-1-yl)]ethanone;CS-0206026;FT-0600709;A-1290;O10277;Q27089400

Chemical Property of N-Acetylindoxyl

Chemical Property:

• Appearance/Colour: Off-white crystals
• Vapor Pressure: 7.42E-05mmHg at 25°C
• Melting Point: 140-142 °C
• Refractive Index: 1.612
• Boiling Point: 332.698 °C at 760 mmHg
• PKA: 9.32±0.40(Predicted)
• Flash Point: 155.011 °C
• PSA: 42.23000
• Density: 1.243 g/cm³
• LogP: 2.00700
• Storage Temp.: Refrigerator
• Solubility.: Acetone, Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 217

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Acetyl-3-hydroxyindole ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1C=C(C2=CC=CC=C21)O
• Uses: N-Acetyl-3-hydroxyindole is a useful synthetic intermediate. Auxin like molecule, used in the preparation of peptidomimetics.

Technology Process of N-Acetylindoxyl

There total 6 articles about N-Acetylindoxyl 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: 83.0%

N,O-diacetylindoxyl (16800-67-2) → 1-(3-hydroxy-1H-indol-1-yl)ethanone (33025-60-4)

Guidance literature:

With sodium sulfite; for 2h; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1021/acs.jmedchem.5b01757

Reference yield:

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → 1-(3-hydroxy-1H-indol-1-yl)ethanone (33025-60-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / water / 16.5 h / 90 °C / Inert atmosphere

2: triethylamine / 21 h / 0 - 80 °C / Inert atmosphere

3: water; Na⁽³⁺⁾*O₄S^(2-) / ethanol / 12 h / 80 °C

With Na⁽³⁺⁾*O₄S^(2-); water; potassium carbonate; triethylamine; In ethanol; water;

Reference yield:

phenylglycine-o-carboxylic acid (612-42-0) → 1-(3-hydroxy-1H-indol-1-yl)ethanone (33025-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / 21 h / 0 - 80 °C / Inert atmosphere

2: water; Na⁽³⁺⁾*O₄S^(2-) / ethanol / 12 h / 80 °C

With Na⁽³⁺⁾*O₄S^(2-); water; triethylamine; In ethanol;

upstream raw materials:

N,O-diacetylindoxyl

indoxyl

acetic anhydride

anthranilic acid

Downstream raw materials:

(1-acetyl-indol-3-yl)-(tetra-O-acetyl-β-D-glucopyranoside)

Refernces

• 1、 -. "CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF". Paragraph 0356. . Retrieved 2015/06/17.
• 2、 -. "N-ARYLSULFONYL-3-AMINOALKOXYINDOLES". Page 56. . Retrieved 2008/06/13.