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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

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

543896-VAR:
543896-BULK:
543896-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK0808
MKBW4651V
MKBL8361V
MKBF7558V
07414TH

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Synthesis and characterization of novel electro-optic chromophores based on 4-hydroxycarbazole.
Zhou T, et al.
Materials Letters, 97, 117-120 (2013)
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
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
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)
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
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