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:
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)
Hayaka Fukuzumi et al.
Carbohydrate polymers, 93(1), 172-177 (2013-03-08)
Various mechanical disintegration conditions in water were applied to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-oxidized cellulose to prepare TEMPO-oxidized cellulose nanofibrils (TOCNs) of uniform widths ∼4 nm but with three different average lengths, 200, 680, and 1100 nm. The viscosity average degrees of polymerization
Akira Isogai et al.
Nanoscale, 3(1), 71-85 (2010-10-20)
Native wood celluloses can be converted to individual nanofibers 3-4 nm wide that are at least several microns in length, i.e. with aspect ratios>100, by TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl radical)-mediated oxidation and successive mild disintegration in water. Preparation methods and fundamental characteristics