Catalog Number
ACM2564832-2
Product Name
2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical (purified by sublimation)
Category
Organic Radicals; Other Material Building Blocks; Battery Materials; Polymerization Reagents
Synonyms
TEMPO Free Radical (purified by sublimation)
Canonical SMILES
CC1(CCCC(N1[O])(C)C)C
InChI
InChI=1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3
InChI Key
QYTDEUPAUMOIOP-UHFFFAOYSA-N
Appearance
Orange to Brown powder to crystal
Application
The 2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical, purified by sublimation and appearing as orange crystals or powder, serves multiple specialized purposes. It plays a key role as a catalytic oxidant in green chemistry, enabling the copper-catalyzed aerobic oxidation of alcohols, which aligns with more sustainable processes. It is also utilized in the iodobenzene diacetate oxidation of nerol to neral and effectively traps styrenyl radicals during the nitroxide-mediated radical polymerization of styrene, which is initiated by benzoyl peroxide. Moreover, this compound contributes to the carboxylation of water-resistant nanofibrillated cellulose films. Its function extends to catalyzing the oxidation of primary alcohols to aldehydes under ambient conditions using a Copper(I)/TEMPO catalyst system. With its strong reactivity and versatility, the compound supports advancements in polymer chemistry, sustainable materials, and fine chemical synthesis.
Storage
Store under inert gas
Covalently-Bonded Unit Count
1
Exact Mass
156.138839g/mol
Hazard Statements
H314 : Causes severe skin burns and eye damage.
MeSH Entry Terms
2,2,6,6-tetramethyl-1-piperidinyloxyl;2,2,6,6-tetramethyl-4-piperidine-N-oxide;2,2,6,6-tetramethylpiperidine-1-oxyl;oxoammonium TPO;TEMPO
Monoisotopic Mass
156.138839g/mol
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.