52602-39-8

Basic information

• Product Name: 9H-Carbazol-4-ol
• Synonyms: 9H-CARBAZOL-4-OL;4-HYDROXYCARBAZOLE;4 HYDROXY 9(H)CARBAZOLE;4-Carbazolol;SKF 106023;4-HYDROXYCARBAZOLE(CARVEDILOL INTERMEDIATE );9H-CARBAZOLE-4-OL;p-HydroxycarBazole
• CAS NO: 52602-39-8
• Molecular Formula: C₁₂H₉NO
• Molecular Weight: 183.21
• EINECS: 258-034-9
• Product Categories: PHARMACEUTICAL INTERMEDIATES;Miscellaneous;(intermediate of carvedilol);Aromatics Compounds;Carbazoles;Carbazoles (for Conduting Polymer Research);Functional Materials;Reagents for Conducting Polymer Research;Carvedilol Intermediate;Aromatics;Heterocycles
• Mol File: 52602-39-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 169-173 °C(lit.)
• Boiling Point: 431.4 °C at 760 mmHg
• Flash Point: 214.7 °C
• Appearance: Tan to cacao/Powder
• Density: 1.362 g/cm₃
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightlty), Methanol (Slightly)
• PKA: 9.87±0.30(Predicted)
• CAS DataBase Reference: 9H-Carbazol-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Carbazol-4-ol(52602-39-8)
• EPA Substance Registry System: 9H-Carbazol-4-ol(52602-39-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 52602-39-8(Hazardous Substances Data)

Usage

Chemical Properties

Light-Yellow Solid

Uses

4-Hydroxy Carbazole (cas# 52602-39-8) is a compound useful in organic synthesis.

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

Upstream product

• 41175-05-7 9-phenylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 529-28-2 4-iodoanisol 
• 577-19-5 2-nitrophenyl bromide 
• 591-20-8 3-Bromophenol 
• 6933-50-2 4-methoxy-9H-carbazole 
• 15128-52-6 1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 7447-39-4 copper(II) chloride 
• 123-91-1 1,4-dioxane 
• 7273-18-9 4-oxo-1,2,3,4,5,6,7,8-octahydro-carbazole 
• 1206-76-4 2-(2'-methoxyphenyl)aniline 
• 86-74-8 9H-carbazole 

Downstream Products

• 6933-50-2 4-methoxy-9H-carbazole 
• 95093-95-1 S-(+)-4-(oxiranylmethoxy)-9H-carbazole 
• 915376-31-7 benzyl 4-hydroxy-9H-carbazole-9-carboxylate 
• 915376-32-8 benzyl 3-bromo-4-hydroxy-9H-carbazole-9-carboxylate 
• 915376-33-9 benzyl 3-bromo-1,4-dioxo-1,4-dihydro-9H-carbazole-9-carboxylate 
• 78859-34-4 NSC 305336 
• 392690-75-4 (+)-(S)-1-bromo-4-(oxiran-2-ylmethoxy)carbazole 
• 95094-00-1 (-)-Carvedilol 

Relevant articles and documents

Direct formation of 4,5-disubstituted carbazolesviaregioselective dilithiation

Carbazoles are widely exploited for their interesting photophysical and electronic properties, however bay (4,5-) functionalization is challenging, and previously inaccessible through carbazole C-H activation. We report a simple methodology which introduces a range of versatile 4,5-functionality, enabling the wider investigation of ring annulation and close proximity effects on carbazole properties.

Synthesis of Glycoborine, Glybomine A and B, the Phytoalexin Carbalexin A and the β-Adrenoreceptor Antagonists Carazolol and Carvedilol

We describe a regioselective synthesis of 4- or 5-substituted carbazoles by oxidative cyclisation of meta-oxygen-substituted N-phenylanilines. Using the regiodirecting effect of a pivaloyloxy group, we prepared 4-hydroxycarbazole, a precursor for the enantiospecific synthesis of the β-adrenoreceptor antagonists (?)-(S)-carazolol (5) and (?)-(S)-carvedilol (6). Regioselective palladium(II)-catalysed cyclisation of different diarylamines led to total synthesis of glycoborine (7) and the first total syntheses of the phytoalexin carbalexin A (8), glybomine A (9) and glybomine B (10). For glybomine B (10), a 5-hydroxycarbazole was converted into the corresponding triflate and utilized for introduction of a prenyl substituent.

COMPOUNDS AND METHODS FOR CARBAZOLE SYNTHESIS

Compounds having bi-cyclic structure comprising a partially unsaturated 6-carbon first cyclic moiety interconnected to a 6-carbon second cyclic moiety second via a divalent linking moiety are provided. The compounds can be used as intermediates compounds in methods for the synthesis of carbazoles and derviatives thereof, including carvedilol, and tricyclic alkylhydroxamates, which do not require Fischer indole synthetic steps. Method of preparing the compounds having bi-cyclic structure are also provided.