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

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

CAS No.:2226-96-2
Molecular Weight:172.24472
Introduction: A free radical scavenger View more+
1. Names and Identifiers
1.1 Name
4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
1.2 Synonyms

(4-Hydroxy-2,2,6,6-tetramethyl-1-piperidinyl)oxidanyl (4-Hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl 1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl- 2,2,6,6-Tetramethyl-4-hydroxy-1-piperidinyloxy radical 2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy 2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy radical 2,2,6,6-Tetramethyl-4-piperidinol 1-oxyl 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine 4-Hydroxy-2,2,6,6-te 4-hydroxy-2,2,6,6-tetramethyl piperidinyloxy,free radical 4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDIN-1-YLOXY 4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy, free radical 4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy,free radical 4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY, FREE RADICAL 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl,TEMPOL 4-Hydroxy-2,2,6,6-tetramethylpiperidine N-oxide 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxy 4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL 4-Hydroxy-2,2,6,6-tetramethylpiperidinooxy radical 4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDINOOXY, FREE RADICAL 4-Hydroxy-2,2,6,6-tetramethylpiperidinooxyl 4-hydroxy-2,2,6,6-tetramethylpiperidinoxy radical 4-Hydroxy-2,2,6,6-tetramethylpiperidinoxyl 4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY 4-hydroxy-2,2,6,6-tetramethyl-piperidinyloxy 4-Hydroxy-TEMPO 4-Hydroxy-TEMPO Free Radical 4-OH-TEMPO 4-Oxypiperidol EINECS 218-761-4 HYDROXY-TEMPO MFCD00006478 nitroxyl2 nr1 NR-I OH-Tempo, 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical Tanol Tempol Tetramethylpiperidinol N-oxyl Tetramethylpiperidino-N-oxyl TMPN

1.3 CAS No.
2226-96-2
1.4 EINECS(EC#)
218-760-9
1.5 Molecular Formula
C9H18NO2 (isomer)
1.6 Inchi
InChI=1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3
1.7 InChkey
UZFMOKQJFYMBGY-UHFFFAOYSA-N
1.8 Canonical Smiles
OC1CC(C)(C)N(O)C(C)(C)C1
1.9 Isomers Smiles
[O]N1C(C)(C)CC(O)CC1(C)C
2. Properties
3.1 Density
1.187
3.1 Melting point
69-73℃
3.1 Boiling point
269
3.1 Refractive index
1.4350 (estimate)
3.1 Flash Point
146
3.1 Precise Quality
172.13400
3.1 PSA
23.47000
3.1 logP
1.28370
3.1 Solubility
1670g/l
3.2 Appearance
orange crystals
3.3 Chemical Properties
solid
3.4 Color/Form
Orange
3.5 PH
8.2 (20g/l, H2O, 20℃)
3.6 Water Solubility
soluble
3.7 Stability
Stable. Incompatible with strong oxidizing agents.
3.8 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 Storage
Keep Cold.
4.2 Usage
A free radical scavenger
4. Safety and Handling
5.1 Symbol
GHS07
5.1 Hazard Codes
Xn
5.1 Signal Word
Warning
5.1 Risk Statements
R22;R36/38
5.1 Safety Statements
S26;S37/39
5.1 Hazard Declaration
H302-H315-H319-H335
5.1 RIDADR
NONH for all modes of transport
5.1 Caution Statement
P261-P305 + P351 + P338
5.1 WGK Germany
1
5.1 RTECS
TN8991000
5.1 Report

Reported in EPA TSCA Inventory.

5.2 Specification

The IUPAC name of?4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy is 1-λ1-oxidanyl-2,2,6,6-tetramethylpiperidin-4-ol. With?CAS registry number 2226-96-2,?it is also named as 2,2,6,6-Tetramethyl-4-piperidinol-N-oxyl.?The product's categories are?analytical chemistry; ESR spectrometry; spin labels.?It is orange crystals which is soluble in ethanol, benzene and other organic solvents, soluble in water. In addition,?this chemical?is?stable and?incompatible with strong oxidizing agents.?Moreover, it should be sealed in the container and stored in the cool and dry?place.??

The other characteristics of this product can be summarized as:?(1)XLogP3-AA: 0.9; (2)H-Bond Donor: 1; (3)H-Bond Acceptor: 2; (4)Rotatable Bond Count: 0; (5)Exact Mass: 172.133754; (6)MonoIsotopic Mass: 172.133754; (7)Topological Polar Surface Area: 24.5; (8)Heavy Atom Count: 12; (9)Formal Charge: 0; (10)Complexity: 159; (11)Covalently-Bonded Unit Count: 1.

Preparation of 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy: It can be obtained by?2,2,6,6-tetramethyl-piperidine-1,4-diol.?This reaction needs reagent?H2O2, Trilon B,?catalytic agent?K2WO4 and solvent?H2O at temperature of?25 °C.

?

Uses of 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy:?It has good?inhibition effect?to acrylic acid esters, methyl acrylate, acrylic acid, acrylonitrile, styrene and?butadiene. And it can react with?benzene-1,2,4-tricarbonyl trichloride?to get?tris(2,2,6,6-tetramethyl-1-oxyl-4-piperidyloxy)trimellitate. This reaction needs reagent?pyridine. The yield is 68%.

When you are using this chemical, please be cautious about it as the following:
It?is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:CC1(CC(CC(N1[O])(C)C)O)C
2.?InChI:InChI=1/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3?
3.?InChIKey:UZFMOKQJFYMBGY-UHFFFAOYAG

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 1053mg/kg (1053mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0536225,

5.3 Toxicity
LD50 oral in rat: 1053mg/kg
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Serious eye damage, Category 1

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H302 Harmful if swallowed

H318 Causes serious eye damage

H373 May cause damage to organs through prolonged or repeated exposure

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P314 Get medical advice/attention if you feel unwell.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Precursor and Product
8. Other Information
8.0 Merck
14,9141
8.1 BRN
1422990
8.2 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.
8.3 Chemical Properties
solid
8.4 Uses
A free radical scavenger
8.5 Uses
Spin label for EPR studies; phase transfer dehydration catalyst; antioxidant; inhibitor of olefin free radical polymerization.
8.6 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.
8.7 Synthesis Reference(s)
Synthetic Communications, 19, p. 3509, 1989 DOI: 10.1080/00397918908052760
8.8 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.
8.9 Usage
Superoxide scavenger with neuroprotective, anti-inflammatory and analgesic effects4-Hydroxy-TEMPO free radical is used as a catalyst and a chemical oxidant by virtue of being a stable radical. It is used for detoxifying reactive oxygen species in medicinal chemistry. It is involved in the catalysis of disproportionation of superoxide and facilitates hydrogen peroxide metabolism. It is used to prepare tris(2,2,6,6-tetramethyl-1-oxyl-4-piperidyloxy)trimellitate by reacting with benzene-1,2,4-tricarbonyl trichloride. Further, it is used as a free radical scavenger and exhibits neuroprotective, anti-inflammatory and analgesic effects. In addition to this, it has good inhibition effect to acrylic acid esters, methyl acrylate, acrylic acid, acrylonitrile, styrene and butadiene.
9. Computational chemical data
  • Molecular Weight:172.24472g/mol
  • Molecular Formula:C9H18NO2
  • Exact Mass:172.133754
  • Monoisotopic Mass:172.133754
  • Complexity:159
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Topological Polar Surface Area:24.5
  • Heavy Atom Count:12
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
10. Question & Answer
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