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758272

Sigma-Aldrich

8-Ethylquinoline N-oxide

97%

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About This Item

Empirical Formula (Hill Notation):
C11H11NO
Molecular Weight:
173.21
MDL number:
MFCD28053538
UNSPSC Code:
12352005
PubChem Substance ID:
329766730
NACRES:
NA.22

Assay

97%

form

solid

reaction suitability

reagent type: oxidant

mp

104-109 °C

storage temp.

2-8°C

SMILES string

CCC1=CC=CC2=C1[N+]([O-])=CC=C2

InChI

1S/C11H11NO/c1-2-9-5-3-6-10-7-4-8-12(13)11(9)10/h3-8H,2H2,1H3

InChI key

LZEBWZDDNNWJJK-UHFFFAOYSA-N

Application

Reactant for the preparation of:
  • α, β-unsaturated enones with catalytic amounts of Gold complexes
  • Synthesis of azetidines (4-membered nitrogen containing heterocycles) through an intramolecular oxidative cyclization in the presence of catalytic amounts of Gold complexes

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBZ3072V
MKBJ9684

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A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes.
Longwu Ye et al.
Angewandte Chemie (International ed. in English), 50(14), 3236-3239 (2011-03-08)
Biao Lu et al.
Journal of the American Chemical Society, 132(40), 14070-14072 (2010-09-22)
Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile α,β-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A

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