2,2,6,6-Tetramethylpiperidinooxy

Names

[ Name ]:
2,2,6,6-Tetramethylpiperidinooxy

[Synonym ]:
Tanan
2,6,6-Tetramethylpiperidine N-oxide
2,2,6,6-Tetramethyl piperidine-N-oxyl
(2,2,6,6-Tetramethyl-1-piperidinyl)oxidanyl
2,2,6,6-tetramethyl-1-piperidinyloxy radical
2,2,6,6-Tetramethylpiperidoxyl
free radical,2,2,6,6-Tetramethylpiperidine 1-oxyl
2,2,6,6-Tetramethyl-1-piperidinyloxy
2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical
1-Piperidinyloxy, 2,2,6,6-tetramethyl-
Piperidinooxy, 2,2,6,6-tetramethyl-
2,2,6,6-Tetramethylpiperidinooxy
Tetramethylpiperidinooxy
T6NTJ AO B1 B1 F1 F1 &&Free Radical
Tanane
tetramethylpiperidinenitroxide
EINECS 219-888-8
(2,2,6,6-Tetramethylpiperidin-1-yl)oxidanyl
TEMPO
2,2,6,6-tetramethylperidinooxy
2,2,6,6-tetramethyl-1-piperidinyloxy,free radical
MFCD00009599
2,2,6,6-Tetramethyl-1-piperidinyloxy,free radical,2,2,6,6-Tetramethylpiperidine 1-oxyl

Biological Activity

[Description]:

Tempo is a classic nitroxide radical and is a selective scavenger of mitochondrial ROS that dismutases superoxide in the catalytic cycle. Tempo induces DNA-strand breakage. Tempo can be used as an organocatalyst for the oxidation of primary alcohols to aldehydes. Tempo has mutagenic and antioxidant effects[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> ROS

[References]

[1]. Du K, et al. Mitochondria-targeted antioxidant Mito-Tempo protects against acetaminophen hepatotoxicity. Arch Toxicol. 2017 Feb;91(2):761-773.

[2]. Guo X, et al. Comparative Genotoxicity of TEMPO and 3 of Its Derivatives in Mouse Lymphoma Cells. Toxicol Sci. 2018 May 1;163(1):214-225.

[3]. Lv H, et al. TEMPO catalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes. Org Biomol Chem. 2020 Apr 22.

[4]. Chen X, et al. Isocitrate dehydrogenase 2 contributes to radiation resistance of oesophageal squamous cell carcinoma via regulating mitochondrial function and ROS/pAKT signalling. Br J Cancer. 2020 May 5.

Chemical & Physical Properties

[ Density]:
1 g/cm3

[ Boiling Point ]:
193°C

[ Melting Point ]:
36-38 °C(lit.)

[ Molecular Formula ]:
C₁₀H₂₁NO?

[ Molecular Weight ]:
156.245

[ Flash Point ]:
154 °F

[ Exact Mass ]:
156.138840

[ PSA ]:
3.24000

[ LogP ]:
2.31290

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Incompatible with strong acids, strong oxidizing agents. Refrigerate.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TN8991900

CHEMICAL NAME :: Piperidinooxy, 2,2,6,6-tetramethyl-

CAS REGISTRY NUMBER :: 2564-83-2

LAST UPDATED :: 199710

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C9-H18-N-O

MOLECULAR WEIGHT :: 156.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-0786-0607S

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-0786-0607S ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LCLo - Lowest published lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4500 mg/m3/2H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-0786-0607S

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-0786-0607S

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H314

[ Precautionary Statements ]:
P280-P305 + P351 + P338-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
C:Corrosive; Xi:Irritant

[ Risk Phrases ]:
R34;R36/37/38

[ Safety Phrases ]:
S26-S36/37/39-S45-S24/25

[ RIDADR ]:
UN 3263 8/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
TN8991900

[ Packaging Group ]:
III

[ Hazard Class ]:
8

[ HS Code ]:
29333999

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 29333999

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