Skip to Content
Merck
CN
All Photos(3)

Documents

701718

Sigma-Aldrich

2-Azaadamantane-N-oxyl

90%

Synonym(s):

AZADO

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C9H14NO
CAS Number:
57625-08-8
Molecular Weight:
152.21
MDL number:
MFCD11656077
UNSPSC Code:
12352000
PubChem Substance ID:
329762314
NACRES:
NA.22

Quality Level

100

Assay

90%

form

powder

reaction suitability

reagent type: oxidant

mp

182-189 °C (D)

storage temp.

2-8°C

SMILES string

[O]N1[C@@H]2C[C@H]3C[C@@H](C2)C[C@@H]1C3

InChI

1S/C9H14NO/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2/t6-,7+,8-,9+

InChI key

BCJCJALHNXSXKE-SPJNRGJMSA-N

Related Categories

General description

2-Azaadamantane-N-oxyl (AZADO), a stable nitroxyl radical, is widely employed as catalyst for the oxidation of alcohols.

Application

2-Azaadamantane-N-oxyl (AZADO) may be employed in the following studies:
  • As catalyst for the oxidation of wood cellulose.
  • As catalyst in the total synthesis of Yaku′amide A, a potential cytotoxin obtained from sponge Ceratopsion sp.
  • As oxidant for the oxidation of (S)-glycidol.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What are the benefits of the organocatalyst 2-Azaadamantane-N-oxyl, Product 701718?

    AZADO (2-azaadamantane N-oxyl) can convert alcohols to their corresopnding carbonyl compounds more effectively than the traditional TEMPO reagent in sterically hindered environments.

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Ming Zhang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(10), 3937-3941 (2015-01-22)
An increased supply of scarce or inaccessible natural products is essential for the development of more sophisticated pharmaceutical agents and biological tools, and thus the development of atom-economical, step-economical and scalable processes to access these natural products is in high
Takefumi Kuranaga et al.
Journal of the American Chemical Society, 135(14), 5467-5474 (2013-03-19)
Here we report the first total synthesis and the complete stereochemical assignment of yaku'amide A. Yaku'amide A (1) was isolated from a sponge Ceratopsion sp. as an extremely potent cytotoxin. Its structure was determined except for the C4-stereochemistry in the
Masatoshi Shibuya et al.
Journal of the American Chemical Society, 128(26), 8412-8413 (2006-06-29)
Development of a stable nitroxyl radical class of catalysts, 2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO, for highly efficient oxidation of alcohols is described. AZADO and 1-Me-AZADO exhibit superior catalytic proficiency to TEMPO, converting various sterically hindered alcohols to the corresponding carbonyl
Takuya Isogai et al.
Biomacromolecules, 11(6), 1593-1599 (2010-05-18)
Curdlan, amylodextrin, and regenerated cellulose fiber were subjected to electromediated oxidation with a 4-acetamido-TEMPO catalyst in a buffer at pH 6.8 without NaClO or NaClO(2). More than 90% of the C6 primary hydroxyls of Curdlan and amylodextrin were converted to

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service