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192694

Sigma-Aldrich

Isoquinoline N-oxide

98%

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About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
1532-72-5
Molecular Weight:
145.16
EC Number:
216-242-7
MDL number:
MFCD00006903
UNSPSC Code:
12352100
PubChem Substance ID:
24851557
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

98%

form

solid

mp

103-105 °C (lit.)

SMILES string

[O-][n+]1ccc2ccccc2c1

InChI

1S/C9H7NO/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

InChI key

RZIAABRFQASVSW-UHFFFAOYSA-N

General description

Photochemical isomerization of isoquinoline N-oxide in methanol or water has been investigated by steady-light irradiation and flash spectroscopy[1]. It is a useful intermediate for isoquinoline derivatives[2]. It causes the oxidation of fullerene C60 under ultrasonic irradiation in air[3].

Application

Isoquinoline N-oxide was used in the synthesis of N-alkoxy isoquinolinium and N-alkoxy 4-phenylpyridinium ion terminated polystyrenes[4].

Storage Class Code

11 - 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
16421HH
11922CH
08119HE
17301EE
16010CE

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The primary photochemical process of isoquinoline N-oxide in hydroxylic solvents.
Ono I and Hata N.
Bulletin of the Chemical Society of Japan, 46, 3658-3662 (1973)
N-alkoxy pyridinium ion terminated polystyrenes: A facile route to photoinduced block copolymerization.
Durmaz YY, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 45(3), 423-428 (2007)
Weon-Bae Ko et al.
Ultrasonics, 42(1-9), 611-615 (2004-03-30)
The reaction of C60 with various amine N-oxides such as 3-picoline N-oxide (Aldrich 98.0%), pyridine N-oxide hydrate (Aldrich 95.0%), quinoline N-oxide (Aldrich 97.0%), isoquinoline N-oxide (Aldrich 98.0%) under ultrasonic irradiation in air at 25-43 degrees C causes the oxidation of
Iodine-mediated electrophilic cyclization of 2-alkynylbenzaldoximes leading to the formation of iodoisoquinoline N-oxides.
Huo Z, et al.
Tetrahedron Letters, 49(38), 5531-5533 (2008)
Oleg V Larionov et al.
Organic letters, 16(3), 864-867 (2014-01-15)
A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method

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