213497
2-Hydroxycarbazole
97%
Synonym(s):
2-Carbazolol
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About This Item
Empirical Formula (Hill Notation):
C12H9NO
CAS Number:
Molecular Weight:
183.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-699-7
Beilstein/REAXYS Number:
135859
MDL number:
Assay:
97%
Form:
solid
Product Name
2-Hydroxycarbazole, 97%
InChI key
GWPGDZPXOZATKL-UHFFFAOYSA-N
InChI
1S/C12H9NO/c14-8-5-6-10-9-3-1-2-4-11(9)13-12(10)7-8/h1-7,13-14H
SMILES string
Oc1ccc2c(c1)[nH]c3ccccc23
assay
97%
form
solid
mp
270-273 °C (lit.)
Quality Level
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Application
2-Hydroxycarbazole was used in the synthesis of isochromene fused carbazol, (4aS,13bR)-2,5,5-trimethyl-3,4,4a,5,8,13b-hexahydroisochromeno[3,4-b]carbazole.
General description
2-Hydroxycarbazole is a compound structurally related to the Ca2+-mobilizing marine toxin, 9-methyl-7-bromoeudistomin. Room temperature electronic absorption and fluorescence spectra of 2-hydroxycarbazole has been studied in concentrated aqueous potassium hydroxide solutions. It undergoes chemoselective N-alkylation using NaH as a base in a THF-DMF solvent system.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Tamanna Mallick et al.
Colloids and surfaces. B, Biointerfaces, 172, 440-450 (2018-09-10)
Six structurally different carbazoles (1-6) were explored as the green reducing agents for the synthesis of the fluorescent Au nanoparticles with tailor-made morphology in anionic (sodium dodecyl sulphate, SDS), cationic (cetyltrimethylammonium bromide, CTAB) and neutral (polyvinylpyrrolidone, PVP) micelle medium. Structure
Nguyen Manh Cuong et al.
Natural product communications, 4(7), 921-924 (2009-09-08)
The first synthesis of isochromene fused carbazols, (4aS, 13bR)-2,5,5-trimethyl-3,4,4a,5,8,13b-hexahydroisochromeno[3,4-b]carbazole (2) and its epi-isomer 3 by condensation of citral and 2-hydroxycarbazole using Ti(OEt)4 and MeAlC12 as catalysts is described.
Chemoselective N-alkylation of 2-hydroxycarbazole as a model for the synthesis of N-substituted pyrrole derivatives containing acidic functions.
Albanese D, et al.
Tetrahedron, 51(19), 5681-5688 (1995)
J Doutheil et al.
Cell calcium, 25(6), 419-428 (1999-12-01)
In the physiological state, protein synthesis is controlled by calcium homeostasis in the endoplasmic reticulum (ER). Recently, evidence has been presented that dividing cells can adapt to an irreversible inhibition of the ER calcium pump (SERCA), although the mechanisms underlying
J M Thomas et al.
The Journal of pharmacology and experimental therapeutics, 298(2), 644-650 (2001-07-17)
2-hydroxycarbazole, a compound structurally related to the Ca2+-mobilizing marine toxin 9-methyl-7-bromoeudistomin, has recently been proposed to activate both type 1 and type 2 ryanodine receptors in skeletal and cardiac muscle, respectively. This study was undertaken to evaluate the activity of
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