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CAS RN: 2564-83-2 | Product Number: T1560

2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical

Purity: >98.0%(GC)(T)
  • TEMPO Free Radical
9   7   ≥40 
4   2   ≥40 

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Product Number T1560
Purity / Analysis Method >98.0%(GC)(T)
Molecular Formula / Molecular Weight C__9H__1__8NO = 156.25 
Physical State (20 deg.C) Solid
Storage Temperature 0-10°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive,Heat Sensitive
CAS RN 2564-83-2
Reaxys Registry Number 1422418
PubChem Substance ID 87577318
Merck Index (14) 9140
MDL Number


Appearance Orange to Brown powder to crystal
Purity(GC) min. 98.0 %
Purity(Iodometric Titration) min. 98.0 %
Solubility in Methanol almost transparency
Properties (reference)
Melting Point 39 °C
Flash point 67 °C
Solubility (soluble in) Methanol
Pictogram Pictogram
Signal Word Danger
Hazard Statements H314 : Causes severe skin burns and eye damage.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P260 : Do not breathe dusts or mists.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P363 : Wash contaminated clothing before reuse.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P405 : Store locked up.
Related Laws:
RTECS# TN8991900
Transport Information:
UN Number (DOT-AIR) UN3263
Class (DOT-AIR) 8
Packing Group (TCI-A) II
HS Number 2933.39.9200
TCI Practical Example: TEMPO Oxidation Utilizing Iodobenzene Diacetate as a Reoxidant

TEMPO Oxidation Utilizing Iodobenzene Diacetate as a Reoxidant

Used Chemicals


To a solution of 1-naphthalenemethanol (306 mg, 2.0 mmol) in dichloromethane (2 mL, 1.0 mol/L) was added TEMPO (31.2 mg, 0.20 mmol), PhI(OAc)2 (709mg, 2.2 mmol) and the mixture was stirred at room temperature for 4 hours. Dichloromethane (12.5 mL), saturated aqueous sodium thiosulfate solution (12.5 mL) was added and the mixture was stirred for 30 minutes. The organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), brine (10 mL) and the organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:100 - 3:97 on silica gel) to give 1-naphthaldehyde as a yellow liquid (291 mg, 93%).

Experimenter’s Comments

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.50).

Analytical Data


1H NMR (400 MHz, CDCl3); δ 10.41 (s, 1H), 9.26 (d, J = 8.9 Hz, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 6.8 Hz, 1H), 7.93 (d, J = 8.9 Hz, 1H), 7.74-7.57 (m, 3H).

Lead Reference

Nitroxyl-radical-catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles


Typical Procedure:
To a solution of N-benzylbenzenesulfonamide (61.8 mg, 0.25 mmol), KBr (14.9 mg, 0.125 mmol), and Na2SO4 (71.0 mg, 0.50 mmol) in MeCN (1.5 mL) is added t-BuOCl (33.9 µL, 0.30 mmol) at room temperature, and the mixture is stirred at room temperature for 1 h. Then, TEMPO (7.8 mg, 0.050 mmol) is added and stirred at room temperature for 30 min. To the solution is added Na2CO3 (26.5 mg, 0.25 mmol), and the mixture is stirred at room temperature for 20 h. Subsequently, TMSCN (93.8 mL, 0.75 mmol) and LiClO4 (2.7 mg, 0.025 mmol) are added to the reaction mixture, and further stirred at room temperature for 22 h. Saturated Na2SO3 aqueous solution (10 mL) is added to the mixture, and the product is extracted with AcOEt (15 mL×3). The organic phase is washed with brine and dried over Na2SO4. The organic phase is concentrated under reduced pressure, and the crude product is purified by column chromatography (hexane : AcOEt = 3 : 1) to give the desired product (67.4 mg, Y. 99%).


Catalytic Oxidation


PubMed Literature

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