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:
Molecular Weight:
156.25
Beilstein:
1422418
EC Number:
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
grade
purum
Assay
≥96.0% (GC)
reaction suitability
reagent type: oxidant
mp
36-38 °C (lit.)
36-39 °C
storage temp.
2-8°C
SMILES string
CC1(C)CCCC(C)(C)N1[O]
InChI
1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3
InChI key
QYTDEUPAUMOIOP-UHFFFAOYSA-N
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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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1C
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 2
Flash Point(F)
152.6 °F - closed cup
Flash Point(C)
67 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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P.L. Anelli et al.
Organic Syntheses, 69, 212-212 (1990)
K.S. Root et al.
Journal of the American Chemical Society, 111, 5405-5405 (1989)
J.F.W. Keana
Chemical Reviews, 78, 37-37 (1978)
E.G. Rozantsev
Free Nitroxyl Radicals (1970)
Jessica M Hoover et al.
Journal of the American Chemical Society, 135(6), 2357-2367 (2013-01-16)
Homogeneous Cu/TEMPO catalyst systems (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) have emerged as some of the most versatile and practical catalysts for aerobic alcohol oxidation. Recently, we disclosed a (bpy)Cu(I)/TEMPO/NMI catalyst system (NMI = N-methylimidazole) that exhibits fast rates and high selectivities, even
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