4-Hydroxyindole Chemical Properties

Melting point:

97-99 °C(lit.)

Boiling point:

245.66°C (rough estimate)

Density 

1.1475 (rough estimate)

vapor pressure 

0.019Pa at 25℃

refractive index 

1.5260 (estimate)

storage temp. 

0-6°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.89±0.40(Predicted)

color 

Dark Yellow to Green-Grey

Water Solubility 

slightly soluble

Sensitive 

Air Sensitive

BRN 

114905

InChIKey

NLMQHXUGJIAKTH-UHFFFAOYSA-N

LogP

1.57 at 25℃

CAS DataBase Reference

2380-94-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339900

MSDS

• Language:English Provider:4-Indolol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Hydroxyindole Usage And Synthesis

Chemical Properties

Off-White Cyrstalline Solid

Uses

4-Hydroxyindole is a Pindolol (P468000) impurity, which is a mixed adrenergic blocker and serotonin 5HT1A-receptor antagonist.

Definition

ChEBI: 4-hydroxyindole is a member of the class of hydroxyindoles that is 1H-indole substituted by a hydroxy group at position 4. It is a member of phenols and a member of hydroxyindoles.

Application

4-Hydroxyindole as simple indoles is the important raw material or intermediate in the synthesis of pharmaceutical products and industrial polymers. It effectively inhibits Abeta peptide-induced amyloid fibril formation and prevent cell death induced by the peptide in culture. It is used for the synthesis of anti-inflammatory angular pyrrolocoumarins.

Preparation

Synthesis of 4-hydroxyindole: Using resorcinol as raw material, 4-oxotetrahydrocoumarone carboxylic acid is prepared by isomerization, catalytic hydrogenation, and cyclization with ethyl bromopyruvate. It was added to methanol solution saturated with ammonia, and the reaction was heated in an autoclave to generate 4-oxotetrahydroindole. Finally, 4-hydroxyindole is obtained by dehydrogenation and isomerization.

General Description

Glucouridination of 4-hydroxyindole by human uridine 5′-diphospho-glucuronosyltransferase has been repotrted.

4-Hydroxyindole(2380-94-1)Related Product Information

• Indole-3-acetic acid
• Indometacin
• Protocatechuic acid
• Indole-3-butyric acid
• Pindolol
• 2-Methylcyclohexylamine
• 4,4'-Oxydianiline
• Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate
• 1-Chloro-3-(1H-indol-4-yloxy)-2-propanol
• 4-Benzyloxyindole-3-carboxaldehyde
• METHYL 4-METHOXY-2-INDOLECARBOXYLATE
• 4-Methoxyindole-3-carboxaldehyde
• 3-HYDROXYINDOLE
• 4-Methoxyindole
• PSILOCIN
• 4-Benzyloxyindole
• 7-HYDROXYINDOLE-2-CARBOXYLIC ACID
• 4-Hydroxy-2-methylindole