CAS 2564-83-2 2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical (purified by sublimation)

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2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical (purified by sublimation)

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Catalog Number

ACM2564832-2

CAS Number

2564-83-2

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)

Molecular Weight

156.25

Molecular Formula

C9H18NO

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

Melting Point

40 °C

Purity

>99.0%(GC)(T)

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

Complexity

136

Covalently-Bonded Unit Count

EC Number

219-888-8

Exact Mass

156.138839g/mol

Formal Charge

Hazard Statements

H314 : Causes severe skin burns and eye damage.

Heavy Atom Count

Log P

1.85 (LogP)

MDL Number

MFCD00009599

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.

Rotatable Bond Count

Signal Word

Danger

UNII

VQN7359ICQ

XLogP3

1.4

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