543896
4-Hydroxycarbazole
95%
Synonym(s):
9H-Carbazol-4-ol
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About This Item
Empirical Formula (Hill Notation):
C12H9NO
CAS Number:
Molecular Weight:
183.21
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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:
It participates as an electron donor for the preparation of nonlinear optical (NLO) chromophores.
- 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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Synthesis and characterization of novel electro-optic chromophores based on 4-hydroxycarbazole.
Zhou T, et al.
Materials Letters, 97, 117-120 (2013)
Pramod V Chavan et al.
Bioorganic chemistry, 85, 475-486 (2019-02-19)
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
Michela Rosini et al.
Journal of medicinal chemistry, 51(15), 4381-4384 (2008-07-09)
Alzheimer's disease (AD) is a multifactorial syndrome with several target proteins contributing to its etiology. To confront AD, an innovative strategy is to design single chemical entities able to simultaneously modulate more than one target. Here, we present compounds that
Synthesis, biological evaluation, and molecular modeling of berberine derivatives as potent acetylcholinesterase inhibitors.
Huang L, et al.
Bioorganic & Medicinal Chemistry, 18(3), 1244-1251 (2010)
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