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543896

Sigma-Aldrich

4-Hydroxycarbazole

95%

Synonym(s):

9H-Carbazol-4-ol

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About This Item

Empirical Formula (Hill Notation):
C12H9NO
CAS Number:
52602-39-8
Molecular Weight:
183.21
EC Number:
258-034-9
MDL number:
MFCD02178385
UNSPSC Code:
12352100
PubChem Substance ID:
24878279
NACRES:
NA.22

assay

95%

mp

169-173 °C (lit.)

SMILES string

Oc1cccc2[nH]c3ccccc3c12

InChI

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

InChI key

UEOHATPGKDSULR-UHFFFAOYSA-N

Related Categories

General description

4-Hydroxycarbazole can be obtained from 1,2,3,4-tetrahydro-4-oxocarbazole via dehydrogenation with freshly prepared Raney nickel.

Application

4-Hydroxycarbazole may be used in the synthesis of the following:
  • 4-(2-bromoethoxy)-9H-carbazole
  • 4-(3-bromopropoxy)-9H-carbazole
  • 4-(4-bromobutoxy)-9H-carbazole
  • 4-(5-bromopentyloxy)-9H-carbazole
  • 4-(6-bromohexyloxy)-9H-carbazole

It participates as an electron donor for the preparation of nonlinear optical (NLO) chromophores.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A series of spirochromenocarbazole tethered 1,2,3-triazoles were synthesized via click chemistry based one-pot, five component reaction between N-propargyl isatins, malononitrile, 4-hydroxycarbazole, aralkyl halides and sodium azide using cellulose supported CuI nanoparticles (Cell-CuI NPs) as the heterogeneous catalyst. Antiproliferative activity of
Kristan H Cleveland et al.
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Huang L, et al.
Bioorganic & Medicinal Chemistry, 18(3), 1244-1251 (2010)
E A Dubois et al.
Journal of medicinal chemistry, 39(17), 3256-3262 (1996-08-16)
A new (radio)iodinated, beta-adrenoceptor ligand, (S)-(-)-4-[3-[(1,1-dimethyl-3-iodo-(2E)-propenyl)-amino]-2- hydroxypropoxy]carbazole (CYBL8E, 1), was prepared. 1 is an iodinated analogue of the high-affinity beta-adrenoceptor antagonist carazolol (2). The asymmetric synthesis was achieved in four steps starting from 4-hydroxycarbazole. The iodine-123-labeled form was obtained by
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