57625-08-8

Basic information

• Product Name: AZADO
• Synonyms: 2-Azaadamantane-N-oxyl;AZADO;2-Azaadamantane-N-oxyl 96%;N-Oxyl-2-azaadamantane
• CAS NO: 57625-08-8
• Molecular Formula: C₉H₁₄NO
• Molecular Weight: 152.22
• Mol File: 57625-08-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 182-189 °C (D)
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: AZADO(CAS DataBase Reference)
• NIST Chemistry Reference: AZADO(57625-08-8)
• EPA Substance Registry System: AZADO(57625-08-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 57625-08-8(Hazardous Substances Data)

Usage

Description

AZADO, also known as 2-Azaadamantane-N-oxyl, is a stable nitroxyl radical that is widely used as a catalyst for the oxidation of alcohols. It is a less hindered nitroxyl radical, which means it exhibits enhanced reactivity compared to other similar compounds like TEMPO.

Uses

Used in Chemical Synthesis:
AZADO is used as a catalyst for the oxidation of wood cellulose, which is an important process in the production of various chemicals and materials from renewable resources.
Used in Pharmaceutical Research:
AZADO is used as a catalyst in the total synthesis of Yaku′amide A, a potential cytotoxin obtained from the sponge Ceratopsion sp. AZADO has potential applications in the development of new drugs and therapies.
Used in Organic Chemistry:
AZADO is used as an oxidant for the oxidation of (S)-glycidol, a key step in the synthesis of various organic compounds.
Used in the Production of Glycerol:
AZADO is used as a catalyst in the production of glycerol, which has a wide range of applications in different industries.
Used in the Food Industry:
AZADO is used as a catalyst in the production of glycerol, which is used as a humectant, sweetener, and preservative in the food industry.
Used in the Pharmaceutical Industry:
AZADO is used as a catalyst in the production of glycerol, which is used as a solvent and vehicle for pharmaceutical formulations.
Used in the Cosmetics Industry:
AZADO is used as a catalyst in the production of glycerol, which is used as a moisturizer and humectant in cosmetics and personal care products.
Used in the Energy Industry:
AZADO is used as a catalyst in the production of glycerol, which can be used as a feedstock for the production of biofuels and other energy-related applications.

Upstream product

• 768-41-2 2-azatricyclo[3.3.1.13,7 ]decane 
• 1155843-79-0 2-azatricyclo[3.3.1.1^3,7]decan-2-ol 
• 66077-97-2 spiro[bicyclo[3.3.1]nonane-3,2'-[1,3]dioxolan]-7-one 
• 770-15-0 bicyclo[3.3.1]nonane-3,7-dione 
• 17933-29-8 7-methylenebicyclo[3.3.1]nonan-3-one 
• 5001-18-3 1,3-adamantandiol 
• 3015-19-8 1-Hydroxy-2-aza-adamantan 
• 905832-09-9 N-benzyloxycarbonyl-2-azaadamantane-1-ol 
• 157521-81-8 7,7-ethylenedioxybicyclo[3.3.1]nonan-3-one oxime 

Downstream Products

• 1352617-40-3 C₁₉H₂₉NO₂ 
• 22627-45-8 3-(3-butenyl)cyclohex-2-en-1-one 
• 1384131-09-2 C₂₃H₂₅NO₂ 

Relevant articles and documents

C?H Activation from Iron(II)-Nitroxido Complexes

The reaction of nitroxyl radicals TEMPO (2,2′,6,6′-tetramethylpiperidinyloxyl) and AZADO (2-azaadamantane-N-oxyl) with an iron(I) synthon affords iron(II)-nitroxido complexes (ArL)Fe(κ1-TEMPO) and (ArL)Fe(κ2-N,O

Practical preparation methods for highly active azaadamantane-nitroxyl- radical-type oxidation catalysts

We have recently disclosed that a less hindered class of nitroxyl radicals, i.e., 2-azaadamantan-N-oxyl (AZADO), 1-Me-AZADO, and 9-azabicyclo[3.3.1]nonan- N-oxyl (ABNO), exhibit marked catalytic activity for the oxidation of alcohols with the aid of environmentally friendly oxidants, offering a green and sustainable option for current alcohol oxidation. Encouraged by their outstanding catalytic performance, we envisioned the development of scalable routes to these radicals that could be extended to the commercialization of these radicals for benchtop use as well as for industrial use as optional reagents that complement TEMPO, the flagship compound of stable nitroxyl radicals. We herein describe short and reproducible preparation methods for AZADO and 1-Me-AZADO, featuring an efficient construction of the 2-azaadamantane skeleton. 1 Introduction 2 1-Me-AZADO and AZADO: First-Generation Syntheses 3 Second-Generation Synthesis of 1-Me-AZADO 4 Synthetic Venture towards 2-Azaadamantane: Second-Generation Synthesis of AZADO 5 Conclusion. Georg Thieme Verlag Stuttgart.

2-Azaadamantane N-oxyl (AZADO) and 1-Me-AZADO: Highly efficient organocatalysts for oxidation of alcohols

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 compounds in excellent yields. Copyright