6-Hydroxyindole Chemical Properties

Melting point:

125-128 °C

Boiling point:

343.2±15.0 °C(Predicted)

Density 

1.327±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly, Heated), Methanol (Slightly)

pka

10.07±0.40(Predicted)

form 

Shiny Crystalline Powder

color 

White to off-white

Cosmetics Ingredients Functions

HAIR DYEING

Cosmetic Ingredient Review (CIR)

6-Hydroxyindole (2380-86-1)

InChI

InChI=1S/C8H7NO/c10-7-2-1-6-3-4-9-8(6)5-7/h1-5,9-10H

InChIKey

XAWPKHNOFIWWNZ-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(O)=C2)C=C1

CAS DataBase Reference

2380-86-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/37/38-51/53-43-41-22

Safety Statements 

37/39-26-61-24-2

RIDADR 

UN 3077

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

HazardClass 

9

PackingGroup 

Ⅲ

HS Code 

29339900

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Aquatic Chronic 2
Eye Dam. 1
Skin Sens. 1

MSDS

• Language:English Provider:ACROS

6-Hydroxyindole Usage And Synthesis

Chemical Properties

White to off-white shiny crystalline powder

Uses

• Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
• Reactant for asymmetrical synthesis of notoamide J as a potential biosynthetic precursor of prenylated indole alkaloids
• Reactant for preparation of (quinolinyloxymethyl)isoxazolecarboxylate esters antituberculosis agents
• Reactant for preparation of indolyl(propanolamine) derivatives as HIV inhibitors
• Reactant for preparation of indoleoxyacetic acid derivatives as peroxisome proliferator-activated receptor agonists
• Reactant for preparation of 1-aroylindole 3-aroylindoles combretastatin A-4 analogs as antitumor agents and tubulin polymerization inhibitors

Synthesis Reference(s)

Journal of Medicinal Chemistry, 35, p. 2419, 1992 DOI: 10.1021/jm00091a010

Synthesis

Regioselective chloroacetylation of 1-pivaloylindole followed by Baeyer-Villiger oxidation offers introduction of an oxygen function into the 6-position of the indole ring. Deacylation of 6-chloroacetyl-1-pivaloylindole gives 6-hydroxyindole. The overall yield of 6-hydroxyindole from indole is 54%.

[1] K. TERANISHI; T. G; S I NAKATSUKA. ChemInform Abstract: Facile Synthesis of 6-Hydroxyindole (VII) and 6-Methoxyindole (IX) via Regioselective Friedel-Crafts Acylation and Baeyer-Villiger Oxidation.[J]. ChemInform, 1995, 26 9. DOI:10.1002/chin.199509120.

6-Hydroxyindole(2380-86-1)Related Product Information

• Indometacin
• Indole-3-butyric acid
• Indole-3-acetic acid
• Indole
• Indoline-2-carboxylic acid
• Indazole-3-carboxylic acid
• 3-HYDROXY-1-PHENYL-6-PYRIDAZONE
• 6-Cyanoindole
• 6-cyanopyridine-3-boronic acid
• 6-CHLOROINDOLE-3-ACETONITRILE
• 6-chloropyrazine-2-carbonitrile
• 6-CHLORO-2,3-DIHYDRO-1H-INDOLE
• 6-Cyanopyridine-2-carboxylic acid
• 6-Chloroindole
• 2,3-DIHYDRO-1H-INDOLE-6-CARBONITRILE HYDROCHLORIDE
• 6-Hydroxyindolin-2-one
• 6-Hydroxyindazole
• 6-Oxo-3H-pyrimidine-4-carboxylic acid