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131652

Sigma-Aldrich

Pyridine N-oxide

95%

Synonym(s):

Pyridine oxide

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About This Item

Empirical Formula (Hill Notation):
C5H5NO
CAS Number:
694-59-7
Molecular Weight:
95.10
Beilstein:
105257
EC Number:
211-774-6
MDL number:
MFCD00006194
UNSPSC Code:
12352100
PubChem Substance ID:
24848028
NACRES:
NA.22
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Assay

95%

form

solid

bp

270 °C (lit.)

mp

62-67 °C (lit.)

SMILES string

[O-][n+]1ccccc1

InChI

1S/C5H5NO/c7-6-4-2-1-3-5-6/h1-5H

InChI key

ILVXOBCQQYKLDS-UHFFFAOYSA-N

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General description

Pyridine N-oxide axle with [2]rotaxanes was synthesized via an anion templated threading-followed-by-stoppering strategy[1].

Application

Pyridine N-oxide was used to study the FTIR spectra of pyridine N-oxide in acetonitrile[2].

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

289.4 °F - closed cup

Flash Point(C)

143 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5351V
WXBF4147V
WXBF0278V
WXBF2220V
WXBD7748V

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Xue Gong et al.
Organic letters, 13(7), 1766-1769 (2011-03-11)
A Pd(II)-catalyzed oxidative coupling between pyridine N-oxides and N-substituted indoles via 2-fold C-H bond activation was achieved with high selectivity using Ag(2)CO(3) as an oxidant.
Jinshui Chen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(30), 7268-7276 (2009-07-07)
Optically active chiral alkyl chlorides are valuable compounds because of their bioactivity and versatile synthetic utility. Accordingly, the ring opening of epoxides with a chloride nucleophile stands as an important goal in asymmetric catalysis. We describe herein recent advances in
Masahito Murai et al.
Chemical communications (Cambridge, England), 48(61), 7622-7624 (2012-06-26)
Gold(I)-catalysed tandem oxygen-transfer/cycloisomerisation reaction of 2-(2-propynyl)pyridine N-oxides provides an atom-economical route to indolizinone frameworks.
Munawar Hussain et al.
Organic letters, 15(1), 54-57 (2012-12-22)
The synthesis of optically active piperidines by enantioselective addition of aryl Grignard reagents to pyridine N-oxides and lithium binolate followed by reduction is reported for the first time. The reaction results in high yields (51-94%) in combination with good ee
Santiago Barroso et al.
Organic letters, 13(3), 402-405 (2010-12-24)
Enantioselective nitrone cycloadditions with 2-alkenoyl pyridine N-oxides as dipolarophiles have been reported. The reaction is catalyzed by Cu(II)-BOX complexes to give the expected isoxazolidine products with high diastereo- and enantioselectivity.
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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