214000
TEMPO
98%
Synonym(s):
2,2,6,6-Tetramethylpiperidine 1-oxyl, 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
UNSPSC Code:
12352119
NACRES:
NA.22
PubChem Substance ID:
EC Number:
219-888-8
Beilstein/REAXYS Number:
1422418
MDL number:
Assay:
98%
Form:
solid
Quality Level
assay
98%
form
solid
reaction suitability
reagent type: oxidant
greener alternative product characteristics
Catalysis
Learn more about the Principles of Green Chemistry.
sustainability
Greener Alternative Product
mp
36-38 °C (lit.)
greener alternative category
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
General description
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.
TEMPO (2,2,6,6-Tetramethylpiperidin-1-oxyl) is a stable free radical commonly used as an oxidizing agent in organic synthesis. Copper/TEMPO has been utilized in the catalytic oxidation of primary alcohols to aldehydes.
Application
TEMPO can be used:
Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air
- As a catalytic oxidant for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.
- As a catalytic oxidant in the iodobenzene diacetae oxidation of nerol to neral.
- For trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene.
- In the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.
Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air
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signalword
Danger
hcodes
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
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Geisslmeir, David; et al.
Monatshefte fur Chemie / Chemical Monthly, 136(9), 1591-1599 (2005)
Solvent effect on (2, 2, 6, 6-Tetramethylpiperidine-1-yl) oxyl (TEMPO): a RISM-SCF-SEDD study.
Fernandez MJF and Sato H.
Theoretical Chemistry Accounts, 130(2-3), 299-304 (2011)
Block copolymer synthesis using a commercially available nitroxide-mediated radical polymerization (NMP) initiator.
Lee NS and Wooley KL.
Material Matters, 5, 8-15 (2010)