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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Quality Level
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
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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
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)
Kristan H Cleveland et al.
PloS one, 14(5), e0217038-e0217038 (2019-05-21)
Carvedilol is reported to prevent cancers in humans and animal models. However, a molecular mechanism has yet to be established, and the extent to which other β-blockers are chemopreventive remains relatively unknown. A comparative pharmacological approach was utilized with the
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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