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371343

Sigma-Aldrich

4-Hydroxy-TEMPO benzoate, free radical

97%

Synonym(s):

4-Hydroxy-TEMPO benzoate, 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl benzoate

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About This Item

Empirical Formula (Hill Notation):
C16H22NO3
CAS Number:
3225-26-1
Molecular Weight:
276.35
Beilstein:
1431263
MDL number:
MFCD00075563
UNSPSC Code:
12352000
PubChem Substance ID:
24863101
NACRES:
NA.22

Assay

97%

form

solid

mp

99-101 °C (lit.)

SMILES string

CC1(C)CC(CC(C)(C)N1[O])OC(=O)c2ccccc2

InChI

1S/C16H22NO3/c1-15(2)10-13(11-16(3,4)17(15)19)20-14(18)12-8-6-5-7-9-12/h5-9,13H,10-11H2,1-4H3

InChI key

MJEDTBDGYVATPI-UHFFFAOYSA-N

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General description

4-Hydroxy-TEMPO benzoate is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative.

Application

4-Hydroxy-TEMPO benzoate was employed as spin probe to investigate the mechanism of synthesis of SBA-15 and to evaluate its surface properties and pore structure by electron paramagnetic resonance spectroscopy (EPR). It was also used for the functionalization of various polydienes (polybutadiene and polyisoprene). Functionalized polydienes were analyzed by gel permeation chromatography.
Recycling catalyst in hypochlorite/bromite-nitroxide oxidizing system for conversion of alcohols to aldehydes, ketones, and carboxylic acids. It circumvents the need to use a catalytic or stoichiometric heavy metal oxidant.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

TEMPO Catalyzed Oxidations

TEMPO (2,2,6,6-Tetramethylpiperidinyloxy or 2,2,6,6-Tetramethylpiperidine 1-oxyl) and its derivatives are stable nitroxy radicals used as catalysts in organic oxidation reactions. TEMPO was discovered by Lebedev and Kazarnovskii in 1960. The stable free radical nature of TEMPO is due to the presence of bulky substituent groups, which hinder the reaction of the free radical with other molecules.

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