5,6-Dihydroxyindole

Base Information

• Chemical Name: 5,6-Dihydroxyindole
• CAS No.: 3131-52-0
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 2933990090
• European Community (EC) Number: 412-130-9
• UNII: Z3OC8499KG
• DSSTox Substance ID: DTXSID20185242
• Nikkaji Number: J434.158I
• Wikidata: Q9207472
• Metabolomics Workbench ID: 38448
• ChEMBL ID: CHEMBL92636
• Mol file: 3131-52-0.mol

Synonyms:5,6-dihydroxyindole

Chemical Property of 5,6-Dihydroxyindole

Chemical Property:

• Vapor Pressure: 2.38E-07mmHg at 25°C
• Melting Point: 140 °C (decomp)
• Refractive Index: 1.802
• Boiling Point: 411.2 °C at 760 mmHg
• PKA: 9.81±0.40(Predicted)
• Flash Point: 202.5 °C
• PSA: 56.25000
• Density: 1.51 g/cm³
• LogP: 1.57910
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

99.9% ^*data from raw suppliers

5,6-Dihydroxyindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; N
• Hazard Codes: Xn,N
• Statements: 22-41-51/53
• Safety Statements: 22-26-36/37/39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=CC(=C(C=C21)O)O

Technology Process of 5,6-Dihydroxyindole

There total 58 articles about 5,6-Dihydroxyindole 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: 98.1%

C8H7NO2 → 1H-indole-5,6-diol (3131-52-0)

Guidance literature:

With sodium dithionite-hydrate; sodium hydrogencarbonate; In water; at 20 - 58 ℃; for 1h; Inert atmosphere;

Reference yield: 95.0%

5,6-dibenzyloxyindole (4790-19-6) → 1H-indole-5,6-diol (3131-52-0)

Guidance literature:

With Pd⁽⁰⁾EnCat; ammonium formate; In N,N-dimethyl-formamide; at 80 ℃; for 0.166667h; Irradiation; microwave;

DOI:10.1016/j.tetlet.2006.12.041

Reference yield: 90.0%

dopachrome (89762-39-0,3571-34-4) → 1H-indole-5,6-diol (3131-52-0)

Guidance literature:

With sodium L-ascorbate; In water; at 20 ℃; for 0.75h; Product distribution / selectivity;

upstream raw materials:

1-(2-amino-4,5-dihydroxyphenyl)-2-ethylamine

5,6-diacetoxyindole

6-hydroxydopamine hydrobromide

dopamine

Downstream raw materials:

5,6-diacetoxyindole

indole-5,6-quinone

2-(2-amino-4,5-dihydroxybenzyl)-6,7-dihydroxy-3-(5,6-dihydroxyindol-3-yl)quinoline

C₂₄H₂₁N₃O₆

Refernces

• 1、 Pezzella, Alessandro,Panzella, Lucia,Crescenzi, Orlando,Napolitano, Alessandra,Navaratman, Suppiah,Edge, Ruth,Land, Edward J.,Barone, Vincenzo,D'Ischia, Marco. "Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: Integrated chemical, pulse radiolytic, and quantum mechanical investigation". . p. 15490 - 15498. Retrieved 2006.
• 2、 Di, Junwei,Bi, Shuping. "Effect of aluminum (III) on the conversion of dopachrome in the melanin synthesis pathway". . p. 1689 - 1696. Retrieved 2003.
• 3、 Hatcher, Lanying Q.,Simon, John D.. "Ultra-low temperature oxidation of 5,6-dihydroxyindole: A novel approach to study synthetic melanogenesis". . p. 608 - 612. Retrieved 2008.
• 4、 Crescenzi,Costantini,Prota. "Evidence for the intermediacy of quinone-methides in the rearrangement of aminochromes to 5,6-dihydroxyindoles". . p. 6095 - 6096. Retrieved 1990.
• 5、 Murphy, Bryan P.,Schultz, Thomas M.. "Synthesis and Physical Properties of 5,6-Dihydroxyindole". . p. 2790 - 2791. Retrieved 1985.
• 6、 -. "Method for efficiently preparing 5,6-dihydroxyindole (by machine translation)". . . Retrieved 2020/04/29.