5,6-Diacetoxyindole

Base Information

• Chemical Name: 5,6-Diacetoxyindole
• CAS No.: 15069-79-1
• Molecular Formula: C12H11 N O4
• Molecular Weight: 233.224
• DSSTox Substance ID: DTXSID70396689
• Nikkaji Number: J534.080B
• Wikidata: Q82197531
• Mol file: 15069-79-1.mol

Synonyms:5,6-Diacetoxyindole;15069-79-1;(6-acetyloxy-1H-indol-5-yl) Acetate;6-(ACETYLOXY)-1H-INDOL-5-YL ACETATE;5,6-Diacetoxy-1H-indole;1H-indole-5,6-diyl diacetate;SCHEMBL1701759;DTXSID70396689;NTOLUQGMBCPVOZ-UHFFFAOYSA-N;MFCD00152051;AKOS015837952;AS-57190;Acetic acid 6-acetoxy-1H-indol-5-yl ester;CS-0318502;D2317;FT-0627232;D-0760;D90042;A884143

Chemical Property of 5,6-Diacetoxyindole

Chemical Property:

• Vapor Pressure: 4.69E-07mmHg at 25°C
• Melting Point: 136.0 to 140.0 °C
• Refractive Index: 1.607
• Boiling Point: 413.8°C at 760 mmHg
• Flash Point: 204°C
• PSA: 68.39000
• Density: 1.316g/cm³
• LogP: 2.01850
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 233.06880783
• Heavy Atom Count: 17
• Complexity: 318

Purity/Quality:

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

5,6-Diacetoxyindole >98.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C2C(=C1)C=CN2)OC(=O)C

Technology Process of 5,6-Diacetoxyindole

There total 20 articles about 5,6-Diacetoxyindole 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: 80.0%

4,5-diacetoxy-2-ethynylaniline (1186113-21-2) → 5,6-diacetoxyindole (15069-79-1)

Guidance literature:

With copper(l) iodide; triethylamine; In toluene; at 130 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jo901259s

Reference yield: 70.0%

(E)-4,5-diacetoxy-2β-dinitrostyrene (99459-14-0) → 5,6-diacetoxyindole (15069-79-1)

Guidance literature:

With hydrogen; acetic acid; platinum on activated charcoal; for 5h; under 775.7 Torr;

DOI:10.1021/jo00350a089

Reference yield: 7.0%

norepinephrine (51-41-2) + acetic anhydride (108-24-7) → 4-[bis-(1H-5,6-diacetoxyindol-2-yl)methyl]-1,2-diacetoxybenzene + 3,4-diacetoxybenzaldehyde (67727-64-4) + 5,6-diacetoxyindole (15069-79-1) + 1-acetyl-3,5,6-triacetoxyindole

Guidance literature:

norepinephrine; With sodium periodate; phosphate buffer; In water; for 0.0833333h; pH=7.4;

acetic anhydride; With pyridine;

DOI:10.1016/j.tet.2005.02.030

upstream raw materials:

(E)-4,5-diacetoxy-2β-dinitrostyrene

acetic anhydride

L-tyrosine

Noradrenochrome

Downstream raw materials:

1H-indole-5,6-diol

5,6-diacetoxyindol-3-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

diphenyl diselenide

bis(2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-β-D-galactopyranosyl)-1,1'-disulfide

Refernces

• 1、 Powell,Heacock. "-". . p. 341. Retrieved 1971.
• 2、 Heacock et al.. "-". . p. 231,237. Retrieved 1961.
• 3、 Pezzella, Alessandro,Crescenzi, Orlando,Panzella, Lucia,Napolitano, Alessandra,Land, Edward J.,Barone, Vincenzo,D'Ischia, Marco. "Free radical coupling of o -semiquinones uncovered". supporting information. p. 12142 - 12149. Retrieved 2013/09/02.