54637-06-8

Basic information

• Product Name: 2,2,6,6-tetramethylpiperidinyl-1-oxide
• Synonyms: TEMPO; 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical; 2,2,6,6-Tetramethyl-1-piperinedinyloxy; 2,2,6,6-Tetramethylpiperidinooxy; 2,2,6,6-tetramethylpiperidin-1-ol; (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl; 2,2,6,6-Tetramethylpiperidine 1-oxyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy
• CAS NO: 54637-06-8
• Molecular Formula: C₉H₁₈NO
• Molecular Weight: 156.2453
• EINECS: 219-888-8
• Mol File: 54637-06-8.mol
• Article Data: 85

Chemical Properties

• Melting Point: 36-40℃
• CAS DataBase Reference: 2,2,6,6-tetramethylpiperidinyl-1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,6,6-tetramethylpiperidinyl-1-oxide(54637-06-8)
• EPA Substance Registry System: 2,2,6,6-tetramethylpiperidinyl-1-oxide(54637-06-8)

Safety Data

• Hazard Codes: C:Corrosive;;
• Statements: R34:; R36/37/38:
• Safety Statements: S24/25:; S26:; S36/37/39:; S45:
• Hazardous Substances Data: 54637-06-8(Hazardous Substances Data)

Usage

Physical form

Red crystalline solid

Common uses

Catalyst in organic synthesis reactions (specifically, oxidation of alcohols to carbonyl compounds)

Selectivity

Oxidizes primary alcohols to aldehydes and secondary alcohols to ketones without affecting other functional groups

Industries of use

Pharmaceutical and polymer industries, as well as academic research laboratories

Benefits

Versatile, efficient, non-toxic, and easy to handle.

Upstream product

• 26864-01-7 2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride 
• 45842-10-2 2,2,6,6-tetramethyl-1-oxo-piperidinium 
• 74205-72-4 [2,3-Bis-(1H-indol-3-yl)-2H-quinoxalin-1-yl]-phenyl-methanone 
• 101391-39-3 1-[2,3-Bis-(1H-indol-3-yl)-3,4-dihydro-2H-quinoxalin-1-yl]-ethanone 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 7031-93-8 2,2,6,6-tetramethylpiperidin-1-ol 
• 67-68-5 dimethyl sulfoxide 
• 109-99-9 tetrahydrofuran 
• 133745-75-2 N-fluorobis(benzenesulfon)imide 
• 34672-82-7 TEMPOH*HCl 
• 494-38-2 acridine orange 
• 2406-25-9 di-tert-butyl nitroxide 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 

Downstream Products

• 54051-40-0 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine 
• 103533-61-5 (5,10,15,20-tetrakis-4-tolylporphyrinato)(methyl)rhodium(III) 
• 441353-11-3 Rh(bocp)CH₃ 

Relevant articles and documents

An Iron(III) Superoxide Corrole from Iron(II) and Dioxygen

A new structurally characterized ferrous corrole [FeII(ttppc)]? (1) binds one equivalent of dioxygen to form [FeIII(O2?.)(ttppc)]? (2). This complex exhibits a 16/18O2-isotope sensitive ν(O-O) stretch at 1128 cm?1 concomitantly with a single ν(Fe-O2) at 555 cm?1, indicating it is an η1-superoxo (“end-on”) iron(III) complex. Complex 2 is the first well characterized Fe-O2 corrole, and mediates the following biologically relevant oxidation reactions: dioxygenation of an indole derivative, and H-atom abstraction from an activated O?H bond.

Transformation of Formazanate at Nickel(II) Centers to Give a Singly Reduced Nickel Complex with Azoiminate Radical Ligands and Its Reactivity toward Dioxygen

The heteroleptic (formazanato)nickel bromide complex LNi(μ-Br)2NiL [LH = Mes-NH-N═C(p-tol)-N═N-Mes] has been prepared by deprotonation of LH with NaH followed by reaction with NiBr2(dme). Treatment of this complex with KC8led to transformation of the formazanate into azoiminate ligands via N-N bond cleavage and the simultaneous release of aniline. At the same time, the potentially resulting intermediate complex L′2Ni [L′ = HN═C(p-tol)-N═N-Mes] was reduced by one additional electron, which is delocalized across the π system and the metal center. The resulting reduced complex [L′2Ni]K(18-c-6) has aS=1/2ground state and a square-planar structure. It reacts with dioxygen via one-electron oxidation to give the complex L′2Ni, and the formation of superoxide was detected spectroscopically. If oxidizable substrates are present during this process, these are oxygenated/oxidized. Triphenylphosphine is converted to phosphine oxide, and hydrogen atoms are abstracted from TEMPO-H and phenols. In the case of cyclohexene, autoxidations are triggered, leading to the typical radical-chain-derived products of cyclohexene.

Method for preparing hindered amine nitroxide free radical compound by alkaline heterogeneous catalysis system

The method comprises the following steps: dissolving a hindered amine compound in an organic solvent; adjusting pH by a carbonate aqueous solution; reacting with an aqueous hydrogen peroxide solution; and generating a hindered amine nitroxide free radical compound (IV). (V) Or (VI). The method is high in universality, and the hindered amine nitroxide free radical compound with various structures is prepared. The method is high in catalytic activity, short in reaction time, high in yield, simple in preparation process and convenient to operate; a high-purity target product can be obtained through simple phase separation, drying and concentration in the post-treatment process; meanwhile, the aqueous solution system and ethyl acetate can be recycled. Small by-products.