86-79-3

Basic information

• Product Name: 2-HYDROXYCARBAZOLE
• Synonyms: AURORA KA-4595;9H-CARBAZOL-2-OL;2-HYDROXYCARBAZOLE;carbazol-2-ol;2-Hydroxycarbazol (9H-Carbazol-2-ol),;2-carbazolol;2-Hydroxy-9H-carbazole;2-Monohydroxycarbazole
• CAS NO: 86-79-3
• Molecular Formula: C₁₂H₉NO
• Molecular Weight: 183.21
• EINECS: 201-699-7
• Product Categories: Intermediates of Dyes and Pigments;Nitrogen cyclic compounds;Building Blocks;Carbazoles;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 86-79-3.mol

Chemical Properties

• Melting Point: 270-273 °C(lit.)
• Boiling Point: 316.88°C (rough estimate)
• Flash Point: 214.7 °C
• Appearance: /
• Density: 1.1261 (rough estimate)
• Vapor Pressure: 4.78E-08mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• PKA: 10.05±0.30(Predicted)
• BRN: 135859
• CAS DataBase Reference: 2-HYDROXYCARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYCARBAZOLE(86-79-3)
• EPA Substance Registry System: 2-HYDROXYCARBAZOLE(86-79-3)

Safety Data

• Hazard Codes: Xi,C,T,F
• Statements: 36/37/38-34
• Safety Statements: 26-36-37/39-45-36/37/39-27
• WGK Germany: 2
• RTECS: FE6355000
• Hazardous Substances Data: 86-79-3(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
2-Hydroxycarbazole is used as a reagent for distinguishing between heparin, heparin derivatives, and other polyuronides of connective tissue. It is also useful for the determination of d-mannuronic acid in heteropolysaccharides.
Used in Organic Synthesis:
2-Hydroxycarbazole is used as a starting material in the synthesis of isochromene fused carbazole, specifically (4aS,13bR)-2,5,5-trimethyl-3,4,4a,5,8,13b-hexahydroisochromeno[3,4-b]carbazole.

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

Upstream product

• 10537-08-3 2-chloro-9H-carbazole 
• 13314-79-9 5,6,7,8-tetrahydro-carbazol-2-ol 
• 166589-60-2 2-ethoxycarbazole 
• 99970-47-5 2'-Azido-biphenyl-4-ol 
• 20323-67-5 mukonal 
• 76834-74-7 2,2-dimethyl-5-(2-methylindol-3-ylmethylene)-1,3-dioxane-4,6-dione 
• 908850-20-4 9H-carbazol-2-yl methanesulfonate 
• 870703-52-9 9H-carbazol-2-yl trifluoromethanesulfonate 
• 908850-21-5 9H-carbazol-2-yl benzenesulfonate 
• 51264-59-6 4-hydroxy-2-nitrobiphenyl 
• 859938-58-2 7-ethoxy-1,2,3,4-tetrahydro-carbazole 
• 90434-59-6 (3-ethoxy-phenyl)-hydrazine 
• 108-94-1 cyclohexanone 
• 1429337-46-1 2'-iodo-[1,1'-biphenyl]-4-ol 

Downstream Products

• 6933-49-9 2-methoxy-9H-carbazole 
• 14501-64-5 2-Hydroxycarbazole-3-carboxylic acid 
• 23077-32-9 2-hydroxy-9H-carbazole-1-carboxylic acid 
• 152365-48-5 3,3-diphenyl-3H-pyrano<3,2-a>carbazole 
• 859831-53-1 2-(benzyloxy)-9H-carbazole 
• 159325-12-9 9-benzyl-2-hydroxycarbazole 
• 51846-67-4 9-methyl-9H-carbazol-2-ol 
• 39027-93-5 2-methoxy-9-methyl-9H-carbazole 
• 287389-06-4 3-(9H-carbazol-2-yloxy)-benzonitrile 
• 586345-76-8 5-benzyloxy-2-{[(9H-carbazol-2-yl)oxy]methyl}-4H-pyran-4-one 
• 586345-80-4 5-benzyloxy-2-{[(9H-carbazol-2-yl)oxy]methyl}-1-methyl-1H-pyridin-4-one 
• 870703-52-9 9H-carbazol-2-yl trifluoromethanesulfonate 
• 908850-21-5 9H-carbazol-2-yl benzenesulfonate 

Relevant articles and documents

Recyclable copper catalyzed nitrogenation of biphenyl halides: A direct approach to carbazoles

A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C-H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle.

Dioxomolybdenum(VI)-catalyzed reductive cyclization of nitroaromatics. Synthesis of carbazoles and indoles

Reductive cyclization of nitrobiphenyls and nitrostyrenes to carbazoles and indoles, respectively, is carried out by triphenylphosphine under mild conditions catalyzed by a dichlorodioxomolybdenum(VI) complex. A one-pot procedure for the synthesis of regioselectively functionalized indoles has been developed from commercially available onitrobenzaldehydes and phosphoranes.

Photo-Fries rearrangement of carbazol-2-yl sulfonates: Efficient tool for the introduction of sulfonyl groups into polycyclic aromatic compounds

Systematic studies on the photo-Fries rearrangement of different 9H-carbazol-2-yl sulfonates 2 have shown that this type of conversion can be readily used for the preparative-scale introduction of alkyl- or arylsulfonyl groups into polycyclic aromatic compounds under very mild conditions. A series of new 1-sulfonyl- (3) or 3-sulfonyl-9H-carbazoles (4) were prepared in medium-to-good yields, and characterized by UV/VIS, 1H-NMR, and 13C-NMR spectroscopy, as well as by elemental analysis. Effects of irradiation wavelength, solvent polarity, presence or absence of O2, and photosensitizers were studied in detail.

Use of ion channel modulating agents

The present invention relates to the use of a particular class of chemical compounds as modulators of SKCa, IKCa and BKCa channels, and to pharmaceutical compositions comprising the SK/IK/BK channel modulating agents.

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.

Flash Vacuum Pyrolysis of 5-(Indol-2- and -3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-diones

Flash vacuum pyrolysis of 5-(indol-2- and -3-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-diones results in the initial formation of indolylmethyleneketenes, which generally either lose carbon monoxide to produce ethynylindoles or undergo -sigmatropic shifts, followed by electrocyclic rearrangements, to yield carbazolols or benzindol-5(1H)-one. 5-(Indol-2-ylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione and the 3-methylindol-2-yl derivative both yield 3H-pyrroloindol-3-ones via a -sigmatropic rearrangement of the initially formed ketene.

MUKONAL, A PROBABLE BIOGENETIC INTERMEDIATE OF PYRANOCARBAZOLE ALKALOIDS FROM MURRAYA KOENIGII

Mukonal, a carbazole alkaloid has been isolated from Murraya koenigii.The structure of the compound has been established as 2-hydroxy-3-formyl carbazole based on physical (UV, IR, 1H NMR, 13C NMR and mass spectrometry) and chemical transformations. - Keywords: Murraya koenigii; Rutaceae; mukonal; carbazole alkaloid.