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701718

Sigma-Aldrich

2-Azaadamantane-N-oxyl

90%

Synonym(s):

AZADO

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50 MG
€191.00
250 MG
€627.00

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50 MG
€191.00
250 MG
€627.00

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

€191.00

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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.[1]

Application

2-Azaadamantane-N-oxyl (AZADO) may be employed in the following studies:
  • As catalyst for the oxidation of wood cellulose.[2]
  • As catalyst in the total synthesis of Yaku′amide A, a potential cytotoxin obtained from sponge Ceratopsion sp.[3]
  • As oxidant for the oxidation of (S)-glycidol.[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8449
BCCK9853
BCCG6141
BCCG6140
BCCF9336

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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
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
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

Questions

1–2 of 2 Questions  

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

    1 answer

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

      Helpful?

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

    1 answer

    1. 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.

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