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Merck
CN

87903

2,2,6,6-Tetramethylpiperidine 1-oxyl

purum, radical, ≥96.0% (GC)

Synonym(s):

2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical, TEMPO

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About This Item

Empirical Formula (Hill Notation):
C9H18NO
CAS Number:
2564-83-2
Molecular Weight:
156.25
EC Number:
219-888-8
UNSPSC Code:
12352000
PubChem Substance ID:
24888968
Beilstein/REAXYS Number:
1422418
MDL number:
MFCD00009599

Key Documents

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InChI key

QYTDEUPAUMOIOP-UHFFFAOYSA-N

InChI

1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

SMILES string

CC1(C)CCCC(C)(C)N1[O]

grade

purum

assay

≥96.0% (GC)

reaction suitability

reagent type: oxidant

mp

36-38 °C (lit.), 36-39 °C

storage temp.

2-8°C

Other Notes

Stable free radical used for radical trapping in mechanistic studies; TEMPO reacts preferentially with carbon-centered radicals; Calalyst used in the oxidation of prim. alcohols to aldehydes with NaOCl

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1C

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 2

flash_point_f

152.6 °F - closed cup

flash_point_c

67 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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E.G. Rozantsev
Free Nitroxyl Radicals (1970)
P.L. Anelli et al.
Organic Syntheses, 69, 212-212 (1990)
J.F.W. Keana
Chemical Reviews, 78, 37-37 (1978)
K.S. Root et al.
Journal of the American Chemical Society, 111, 5405-5405 (1989)
M Zareba et al.
Free radical biology & medicine, 101, 446-454 (2016-11-15)
Macular xanthophylls (MXs) lutein and zeaxanthin are dietary carotenoids that are selectively concentrated in the human eye retina, where they are thought to protect against age-related macular degeneration (AMD) by multiple mechanisms, including filtration of phototoxic blue light and quenching
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