7384-07-8

Basic information

• Product Name: 3-hydroxycarbazole
• Synonyms: 3-hydroxycarbazole;9H-carbazol-3-ol
• CAS NO: 7384-07-8
• Molecular Formula: C₁₂H₉NO
• Molecular Weight: 183.21
• Product Categories: Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 7384-07-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 256-257 °C
• Boiling Point: 431.4°C at 760 mmHg
• Flash Point: 214.7°C
• Appearance: /
• Density: 1.362g/cm³
• Vapor Pressure: 4.78E-08mmHg at 25°C
• Refractive Index: 1.815
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane, DMSO (Slightly), Ethyl Acetate, Methanol (Slightly)
• PKA: 9.98±0.30(Predicted)
• CAS DataBase Reference: 3-hydroxycarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxycarbazole(7384-07-8)
• EPA Substance Registry System: 3-hydroxycarbazole(7384-07-8)

Safety Data

• Hazardous Substances Data: 7384-07-8(Hazardous Substances Data)

Usage

Description

3-Hydroxycarbazole, also known as Carbazol-3-ol, is a metabolite of N-methylcarbazole found in mammals. It is a beige solid with mutagenic properties, which means it has the potential to cause changes in the genetic material of an organism.

Uses

Used in Pharmaceutical Industry:
3-Hydroxycarbazole is used as a pharmaceutical compound for its mutagenic properties. It is utilized in the development of drugs that target genetic mutations, potentially leading to novel treatments for various diseases and conditions.
Used in Chemical Research:
As a chemical compound with unique properties, 3-Hydroxycarbazole is used as a research material in the field of chemistry. It can be employed in the study of mutagenesis, chemical reactions, and the development of new chemical compounds with potential applications in various industries.
Used in Environmental Studies:
Due to its mutagenic properties, 3-Hydroxycarbazole can be used in environmental studies to assess the impact of pollutants and other environmental factors on the genetic material of living organisms. This can help in understanding the long-term effects of environmental exposure and contribute to the development of strategies for environmental protection and remediation.

InChI:InChI=1/C12H9NO/c14-8-5-6-12-10(7-8)9-3-1-2-4-11(9)13-12/h1-7,13-14H

Upstream product

• 18992-85-3 3-methoxycarbazole 
• 86-74-8 9H-carbazole 
• 13220-42-3 6-methoxy-3-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 589-92-4 1-methylcyclohexan-4-one 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 104-94-9 4-methoxy-aniline 
• 108-86-1 bromobenzene 
• 100717-42-8 6-ethoxy-1,2,3,4-tetrahydro-carbazole 
• 1592-95-6 3-bromo-9H-carbazole 
• 361434-24-4 3-(tert-butyl-dimethyl-silanyloxy)-carbazole-9-carboxylic acid ethyl ester 
• 215853-89-7 ethyl 2-nitroindole-1-carboxylate 
• 13070-45-6 6-Methoxy-1,2,3,4-tetrahydrocarbazole 
• 104917-94-4 9-methyl-3H-pyrrolo<1,2-a>indol-3-one 
• 361434-23-3 ethyl 3-hydroxy-9H-carbazole-9-carboxylate 

Relevant articles and documents

Diels-Alder reactions of 2- and 3-nitroindoles. A simple hydroxycarbazole synthesis

A Diels-Alder reaction of 3- and 2-nitroindoles with Danishefsky's diene gives the expected 2- and 3-hydroxycarbazoles in very good to excellent yields (73-91%) and with apparent complete regioselectivity.

TEMPO-mediated late stage photochemical hydroxylation of biaryl sulfonium salts

The late stage photochemical hydroxylation of biaryl sulfonium salts was enabled with a TEMPO derivative as a simple oxygen source, in metal free conditions. The scope and mechanism of this exceptionally simple synthetic method, which constructs important arylated phenols from aromatic C-H bonds, are herein discussed.

Cis-Dihydroxylation of Tricyclic Arenes and Heteroarenes Catalyzed by Toluene Dioxygenase: A Molecular Docking Study and Experimental Validation

Molecular docking studies of toluene dioxygenase led to the prediction that angular and lateral cis-dihydroxylation of tricyclic arene and heteroarene substrates could occur. Biotransformations of biphenylene, dibenzofuran, carbazole and dibenzothiophene, using Pseudomonas putida UV4 whole cells, expressing toluene dioxygenase, confirmed that both angular and lateral cis-dihydroxylation had occurred in the predicted regioselective and stereoselective manner. The toluene dioxygenase-catalysed (Pseudomonas putida UV4) biotransformation of dibenzofuran was optimized, to produce 1,2-dihydrodibenzofuran-1,2-diol as the major metabolite in excellent yield. 2-Hydroxydibenzofuran, resulting from dehydration of 1,2-dihydrodibenzofuran-1,2-diol, was also found to undergo cis- dihydroxylation to give a very minor cis-dihydrodiol metabolite. The enantiopurity (>98% ee) and (1R,2S) absolute configuration of the major dibenzofuran cis -dihydrodiol was rigorously established by catalytic hydrogenation and formation of methoxy(trifluoromethyl)phenylacetate derivatives and by X-ray crystallography of an epoxide derivative. Biotransformation of carbazole yielded anthranilic acid as the major metabolite and was consistent with angular cis-dihydroxylation. Synthesis of a cis- diol epoxide derivative showed that the main cis-dihydrodiol metabolite of dibenzofuran has potential in the chemoenzymatic synthesis of natural products. (Figure presented.).