426369
TEMPO
purified by sublimation, 99%
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:
Quality Level
assay
99%
form
solid
purified by
sublimation
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
For a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our technology spotlight.
Application
Stable nitroxide radical useful in controlling living polymerizations
TEMPO (2,2,6,6-Tetramethyl-1-piperidinyloxy) was used for trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene. TEMPO-mediated oxidation was employed for the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.
Features and Benefits
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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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Block copolymer synthesis using a commercially available nitroxide-mediated radical polymerization (NMP) initiator.
Lee NS and Wooley KL.
Material Matters, 5, 8-15 (2010)
Soham Maity et al.
Journal of the American Chemical Society, 135(9), 3355-3358 (2013-02-15)
Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective
Xiaolong Liu et al.
The Journal of organic chemistry, 78(17), 8531-8536 (2013-08-16)
Imidazolium salts bearing TEMPO groups react with commercially available copper powder affording Cu-NHC complexes. The in situ generated Cu-NHC-TEMPO complexes are quite efficient catalysts for aerobic oxidation of primary alcohols into aldehydes. The catalyst is easily available, and various primary