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Sigma-Aldrich

8-Isopropylquinoline N-oxide

97%

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Synonym(s):
8-Isopropylquinoline 1-oxide
Empirical Formula (Hill Notation):
C12H13NO
CAS Number:
1246242-17-0
Molecular Weight:
187.24
MDL number:
MFCD22200535
UNSPSC Code:
12352005
PubChem Substance ID:
329766449
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.644

density

1.134 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CC(C)c1cccc2ccc[n+]([O-])c12

InChI

1S/C12H13NO/c1-9(2)11-7-3-5-10-6-4-8-13(14)12(10)11/h3-9H,1-2H3

InChI key

LYLSTLGFFOQSKE-UHFFFAOYSA-N

Application

8-Isopropylquinoline N-oxide can be used as a reagent:
  • In the oxidative cyclization of diynes in the presence of gold catalyst.
  • For the preparation of pyrrolo[3,4-c]quinolin-1-ones by asymmetric alkyne oxidation of chiral N-propargyl ynamides in the presence of a copper catalyst.
  • In the synthesis of 8-(1-methylethyl)-2-[(4-methylphenyl)sulfonyl]- quinoline by deoxygenative and selective sulfonylation with sodium p-toluenesulfinate using iodine/TBHP as a catalyst.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Recent advances in catalytic asymmetric intermolecular oxidation of alkynes
Shen W-B and Tang X-T
Organic & Biomolecular Chemistry, 17(30), 7106-7113 (2019)
Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines
Sumunnee L, et al.
European Journal of Organic Chemistry, 2017(5), 1025-1032 (2017)
Pascal Nösel et al.
Journal of the American Chemical Society, 135(41), 15662-15666 (2013-09-21)
In the presence of a gold catalyst an unprecedented oxidative cyclization of diynes takes place. The reaction cascade is initiated by an oxygen transfer from a N-oxide onto a gold-activated alkyne. The formed α-oxo carbene is transferred across the second

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