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168696

Sigma-Aldrich

4-Hydroxy-1-methyl-2(1H)-quinolone

98%

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About This Item

Fórmula empírica (notación de Hill):
C10H9NO2
Número de CAS:
1677-46-9
Peso molecular:
175.18
EC Number:
216-830-3
MDL number:
MFCD00024052
UNSPSC Code:
12352100
PubChem Substance ID:
24850250
NACRES:
NA.22

assay

98%

form

powder

mp

269-271 °C (lit.)

SMILES string

CN1C(=O)C=C(O)c2ccccc12

InChI

1S/C10H9NO2/c1-11-8-5-3-2-4-7(8)9(12)6-10(11)13/h2-6,12H,1H3

InChI key

RTNPPPQVXREFKX-UHFFFAOYSA-N

Application

4-Hydroxy-1-methyl-2(1H)-quinolone was used as nucleophile in electrochemical oxidation of catechols and the reaction was studied by cyclic voltammetry and controlled-potential coulometry. It was used in ceric ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds to yield substituted dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones and dihydrofurophenalenones. It was used in the synthesis of :
  • 3-(4-methoxybenzyl)-4-hydroxy-1-methylquinolinone
  • 3-(benzo[d][1,3]dioxol-5-ylmethyl)-4-hydroxy-1-methylquinolin-2(1H)-one
  • 3-(4-chlorobenzyl)-4-hydroxy-1-methylquinolin-2(1H)-one
  • 3,3′-bis(4-chlorobenzylidene)-1,10-methylquinolin-2,20-(1H)-one

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Mechanistic study of electrochemical oxidation of catechols in the presence of 4-hydroxy-1-methyl-2 (1H)-quinolone: Application to the electrochemical synthesis.
Fakhari AR, et al.
Electrochimica Acta, 50(27), 5322-5328 (2005)
Iridium catalysed alkylation of 4-hydroxy coumarin, 4-hydroxy-2-quinolones and quinolin-4 (1H)-one with alcohols under solvent free thermal conditions.
Grigg R, et al.
Tetrahedron, 65(36), 7468-7473 (2009)
Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1, 3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products.
Lee YR, et al.
Tetrahedron, 56(45), 8845-8853 (2000)
Michael B Hicks et al.
The Analyst, 142(3), 525-536 (2017-01-18)
The use of a coulometric array detector in tandem with HPLC-UV was evaluated for the absolute quantitation of pharmaceutical compounds without standards, an important capability gap in contemporary pharmaceutical research and development. The high-efficiency LC flow-through electrochemical detector system allows
Mohankumar Saraladevi Resmi et al.
FEBS letters, 589(3), 332-341 (2015-01-06)
Type III polyketide synthases (PKSs) catalyze the biosynthesis of various medicinally important secondary metabolites in plants, but their role in growth and stress response is unclear. Here, we overexpressed quinolone synthase (QNS) from bael in tobacco. QNS-overexpressing plants showed an

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