ChemicalBook > CAS DataBase List > 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy

Product Name
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
CAS No.
2226-96-2
Chemical Name
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
Synonyms
TEMPOL;4-OH-TEMPO;4-HYDROXY-TEMPO;Inhibitor 701;ZJ-701;TMPN;HYDROXY-TEMPO;Polymerization inhibitor 701;Tetramethylpiperidinol N-oxyl;4-hydroxy-2,2,6,6-tetramethylpiperidinoxyl
CBNumber
CB5782374
Molecular Formula
C9H18NO2*
Formula Weight
172.24
MOL File
2226-96-2.mol
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4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Property

Melting point:
69-71 °C(lit.)
Boiling point:
302.58°C (rough estimate)
Density 
1.0402 (rough estimate)
vapor pressure 
0.025Pa at 20℃
refractive index 
1.4350 (estimate)
Flash point:
146°(295°F)
storage temp. 
2-8°C
solubility 
1670g/l
form 
Crystals or Crystalline Powder
pka
5.07[at 20 ℃]
color 
Orange
PH
8.2 (20g/l, H2O, 20℃)
Water Solubility 
soluble
Merck 
14,9141
BRN 
1422990
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
FAPCFNWEPHTUQK-UHFFFAOYSA-N
LogP
0.56 at 25℃
CAS DataBase Reference
2226-96-2(CAS DataBase Reference)
NIST Chemistry Reference
1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-(2226-96-2)
EPA Substance Registry System
1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl- (2226-96-2)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38-36/38
Safety Statements 
26-36-37/39-36/37/39-27
WGK Germany 
1
RTECS 
TN8991000
TSCA 
Yes
HS Code 
29333999
Hazardous Substances Data
2226-96-2(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 1053mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.40130
Product name
4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl
Purity
(free radical) for synthesis
Packaging
25G
Price
$87.4
Updated
2024/03/01
Sigma-Aldrich
Product number
8.40130
Product name
4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl
Purity
(free radical) for synthesis
Packaging
100G
Price
$250
Updated
2024/03/01
Sigma-Aldrich
Product number
176141
Product name
4-Hydroxy-TEMPO
Purity
97%
Packaging
1g
Price
$34.2
Updated
2024/03/01
Sigma-Aldrich
Product number
176141
Product name
4-Hydroxy-TEMPO
Purity
97%
Packaging
5g
Price
$98
Updated
2024/03/01
TCI Chemical
Product number
H0865
Product name
4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical
Purity
>98.0%(GC)
Packaging
5g
Price
$57
Updated
2024/03/01
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4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Chemical Properties,Usage,Production

Description

TEMPOL is a piperidine nitroxide and spin label with superoxide dismutase (SOD) mimetic activity. It inhibits lipid peroxidation in rat liver microsomes with 50% inhibition of microsomal lipid peroxidation (IP50) values of 117, 61, and 381 μM for peroxidation induced by iron plus NADPH, iron plus ascorbate, and t-butylhydroperoxide, respectively. TEMPOL (1 mM) inhibits production of superoxide anions by 92% via a xanthine-xanthine oxidase reaction in vitro. It reduces mean arterial pressure and heart rate in spontaneously hypertensive rats (ED50s = 70 and 63 μmol/kg, respectively) when administered intravenously. TEMPOL is a cell-permeable spin label that has been used to quantify intracellular oxygen in various cell types by electron spin resonance (ESR) spectroscopy.

Chemical Properties

solid

Uses

A free radical scavenger

Uses

Tempol, a water-soluble piperidine nitroxide derivative having nonspecific radical-scavenging and superoxide dismutase (SOD) activity, protects cultured aerobic, but not hypoxic, cells against radiation-induced killing. Protection does not depend on intracellular thiols and does not involve O2-depletion. Tempol reacts with peroxyl radicals and can also oxidize DNA-bound metal ions, thereby interfering with OH? generation.

Uses

Spin label for EPR studies; phase transfer dehydration catalyst; antioxidant; inhibitor of olefin free radical polymerization.

Application

In biochemical research, 4-hydroxy-TEMPO has been investigated as an agent for limiting reactive oxygen species.  It catalyzes the disproportionation of superoxide, facilitates hydrogen peroxide metabolism, and inhibits Fenton chemistry.4-Hydroxy-TEMPO, along with related nitroxides, are being studied for their potential antioxidant properties.On an industrial-scale 4-hydroxy-TEMPO is often present as a structural element in hindered amine light stabilizers, which are commonly used stabilizers in plastics, it is also used as a polymerisation inhibitor, particularly during the purification of styrene. 

Synthesis Reference(s)

Synthetic Communications, 19, p. 3509, 1989 DOI: 10.1080/00397918908052760

General Description

4-Hydroxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. It is a low-molecular weight compound and has been proposed as superoxide dismutase mimic.

Flammability and Explosibility

Non flammable

Biological Activity

Superoxide scavenger that displays neuroprotective, anti-inflammatory and analgesic effects.

storage

Store at -20°C

References

1) Lipman et al. (2006), Neuroprotective effects if the stable nitroxide compound Tempol in 1-methyl-4-phenylpyridinium ion-induced neurotoxicity in the Nerve Growth Factor-differentiated model of pheochromocytoma PC12? cells; Eur. J. Pharmacol., 549 50 2) Guron et al. (2006), Acute effects of the superoxide dismutase mimetic tempol on split kidney function in two-kidney one-clip hypertensive rats; J. Hypertens., 24 387 3) Samuni and Barenholz (1997), Gamma-irradiation damage to liposomes differing in composition and their protection by nitroxides; Free Radic. Biol. Med., 23 972 4) Bernardy et al. (2017), Tempol, a Superoxide Dismutase Mimetic Agent, Inhibits Superoxide Anion-Induced Inflammatory Pain in Mice; Biomed. Res. Int., 2017 9584819 5) De Blasio et al. (2017), The superoxide dismutase mimetic tempol blunts diabetes-induced upregulation of NADPH oxidase and endoplasmic reticulum stress in a rat model of diabetic nephropathy; Eur. J. Pharmacol., 807 12

4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy 2226-96-2
Price
US $99.00-66.00/kg
Min. Order
0.0010000000474974513kg
Purity
99%
Supply Ability
5000
Release date
2024-08-19
Hebei Zhuanglai Chemical Trading Co Ltd
Product
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy 2226-96-2
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 ton
Release date
2024-11-15
Jinan Finer Chemical Co., Ltd
Product
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy 2226-96-2
Price
US $3.00/kg
Min. Order
1 mkg
Purity
99.5%
Supply Ability
500mt
Release date
2019-03-14

2226-96-2, 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxyRelated Search:

Haloperidol CHLOROPHOSPHONAZO III 1,2,2,6,6-Pentamethyl-4-piperidinol 2,2,6,6-Tetramethyl-4-piperidinol Drag-reduction agent Triacetonediamine 2,2,6,6-Tetramethylpiperidine Diethyl bis(2-hydroxyethyl)aminomethylphosphonate 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide 9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide Octabenzone Piperazine-2-carboxylic acid dihydrochloride Tri(4-isopropylphenyl) phosphate 3-Hydroxyphenylphosphinyl-propanoic acid Triphenyl phosphate UV-1164 Tri-(4-hydroxy-TEMPO) phosphite SW606

  • HYDROXY-TEMPO
  • 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL
  • 4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY
  • 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL
  • 4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDIN-1-YLOXY
  • 4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY, FREE RADICAL
  • 4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY, FREE RADICAL
  • 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY
  • 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY FREE RADICAL
  • 4-HYDROXY-TEMPO
  • 4-HYDROXY-TEMPO, FREE RADICAL
  • 4-OH-TEMPO
  • 2,2,6,6-Tetramethyl-4-hydroxypiperidine 1-oxyl
  • 4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy, free radical
  • 4-Hydroxy-TEMPO Styrene,Acrylates+Acrylics polymerisation inhibitor
  • 2,2,6,6-TETRAMETHYL-4-HYDROXY-1-PIPERIDINYLOXY
  • 2,2,6,6-TETRAMETHYL-4-PIPERIDINOL 1-OXYL
  • 4-hydroxy-2,2,6,6-tetramethylpiperidinoxyl
  • 2,2,6,6-Tetramethyl-4-piperidinol-1-oxide
  • 4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl(4-Hydroxy-TEMPO,freeradical)
  • 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-
  • 4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINYLOXY (TMHPO .)
  • 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL(4-HYDROXYTEMPO)
  • Dipyridamole oxide
  • ZJ-701
  • 4-Hydroxy-2,2,6,6-tetramethyl piperidinyloxy free
  • 4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDIN-1-YLOXY / 4-HYDROXY-TEMPO, FREE RADICAL
  • 2,2,6,6-TetraMethyl-4-hydroxy-1-piperidinyloxy Radical
  • Alcoholpiperidine nitroxides
  • 4-Hydroxy-TEMPO 97%
  • Piperidol oxide
  • 2,2,6,6-Tetramethyl-4-piperidinol 1-oxyl, free radical
  • 4-Hydroxy-2,2,6,6-tetramethylpiperidineN-oxide≥ 99% (GC)
  • SUBSTITUTED PIPERIDINYLOXY PYRAZINYL DER
  • 4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (free radical) for synthesis
  • 2,2,6,6-Tetramethyl-4-hydroxypiperidin-1-oxyl
  • 2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy
  • 2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy radical
  • 2,2,6,6-Tetramethyl-4-hydroxypiperidyl 1-oxyl
  • 2,2,6,6-Tetramethyl-4-oxypiperidine-1-oxyl
  • 2,2,6,6-Tetramethyl-4-piperidinol nitroxide
  • 2,2,6,6-Tetramethyl-4-piperidinol N-oxyl
  • 2,2,6,6-Tetramethyl-4-piperidinol-1-oxy
  • 2,2,6,6-tetramethyl-4-piperidinol-n-oxyl
  • 2,2,6,6-Tetramethyl-4-piperindiol 1-oxyl
  • 2,2,6,6-Tetramethylpiperidine-N-oxyl-4-ol
  • 2,2,6,6-Tetramethylpiperidinol-4-oxyl-1
  • 1-Oxyl-2,2,6,6-tetramethyl-4-piperidinol
  • 2,2,4,4-Tetramethyl-4-Piperidinol N-oxide
  • 2,2,6,6-Tetramethyl-1,4-piperidinediol
  • 4-Hydroxy-2,2,6,6-tetramethyl-piperidine1-oxide
  • 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxy
  • 4-hydroxy-2,2,6,6-tetramethyl-piperidinoox
  • 4-Hydroxy-2,2,6,6-tetramethylpiperidinooxy radical
  • TEMPOL
  • Polymerization inhibitor 701
  • 4-hydroxy-2,2,6,6,-tetramethylpiperimyloxy
  • 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinylox