214000 Aldrich

TEMPO Green Alternative


Synonym: 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical, 2,2,6,6-Tetramethylpiperidine 1-oxyl, TEMPO

  • CAS Number 2564-83-2

  • Empirical Formula (Hill Notation) C9H18NO

  • Molecular Weight 156.25

  •  Beilstein Registry Number 1422418

  •  EC Number 219-888-8

  •  MDL number MFCD00009599

  •  PubChem Substance ID 24852819

  • Popular Documents:  FTIR (PDF)  



Related Categories Chemical Synthesis, Others, Oxidizing Agents, Radical Chemistry, Stable Radicals,
assay   98%
greener alternative product characteristics   Catalysis
Learn more about the Principles of Green Chemistry.
mp   36-38 °C(lit.)
storage temp.   2-8°C



1, 5, 25 g in glass bottle


Catalytic oxidant for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.

Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air

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.

General description

Copper/TEMPO has been utilized in the catalytic oxidation of primary alcohols to aldehydes.1

Price and Availability

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Safety & Documentation

Safety Information

GHS05  GHS05
Signal word 
Hazard statements 
Precautionary statements 
UN 3263 8 / PGII
WGK Germany 
Flash Point(F) 
152.6 °F
Flash Point(C) 
67 °C

Protocols & Articles


Stahl Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Stahl Group – Professor Product Portal
Keywords: Aerobic, Catalysis, Dehydrogenation, Filtration, Oxidations, Pharmaceutical, Purification

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 discovere...
Keywords: Aerobic, Capillary electrophoresis, Catalysis, Chromatography, Coupling reactions, Oxidations, Polymerization reactions, Size-exclusion chromatography, Solvents

Peer-Reviewed Papers


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1. Geisslmeir, David; et al. Monatsh. Chem 136(9), 1591-1599, (2005)

Organic Synth. 83, 18, (2006)

Solvent effect on (2, 2, 6, 6-Tetramethylpiperidine-1-yl) oxyl (TEMPO): a RISM-SCF-SEDD study. Fernandez MJF and Sato H. Theor. Chem. Acc. 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)

Surface functionalized nanofibrillar cellulose (NFC) film as a platform for immunoassays and diagnostics. Orelma H, Filpponen I, Johansson LS, et al. Biointerphases 7(1-4), 61, (2012)


Influence of TEMPO-oxidized cellulose nanofibril length on film properties. Fukuzumi H, Saito T, and Isogai A Carbohydr. Polym. 93(1), 172-7, (2013)


TEMPO-oxidized cellulose nanofibers. Isogai A, Saito T, and Fukuzumi H Nanoscale 3(1), 71-85, (2011)


Probing the antimalarial mechanism of artemisinin and OZ277 (arterolane) with nonperoxidic isosteres and nitroxyl radicals. Matthias A Fügi et al Antimicrob. Agents Chemother. 54, 1042-6, (2010)


Unrestricted Hartree-Fock based on the fragment molecular orbital method: energy and its analytic gradient. Nakata H, Fedorov DG, Nagata T, et al. J. Chem. Phys. 137(4), 044110, (2012)


The nitroxide TEMPO is an efficient scavenger of protein radicals: cellular and kinetic studies. Pattison DI, Lam M, Shinde SS, et al. Free Radic. Biol. Med. 53(9), 1664-74, (2012)


Mass spectrometric characterization of glucuronides formed by a new concept, combining Cunninghamella elegans with TEMPO. Rydevik A, Bondesson U, Thevis M, et al. J. Pharm. Biomed. Anal. 84, 278-84, (2013)


Effect of the addition of two superoxide dismutase analogues (Tempo and Tempol) to alpaca semen extender for cryopreservation. Acosta AS, Vargas SE, Cuya MV, et al. Theriogenology 79(5), 842-6, (2013)


Fast and continuous preparation of high polymerization degree cellulose nanofibrils and their three-dimensional macroporous scaffold fabrication. Song J, Tang A, Liu T, et al. Nanoscale 5(6), 2482-90, (2013)


Mechanism of copper(I)/TEMPO-catalyzed aerobic alcohol oxidation. Hoover JM, Ryland BL, and Stahl SS J. Am. Chem. Soc. 135(6), 2357-67, (2013)


Efficient and stereoselective nitration of mono- and disubstituted olefins with AgNO2 and TEMPO. Maity S, Manna S, Rana S, et al. J. Am. Chem. Soc. 135(9), 3355-8, (2013)


Oxidized cellulose--survey of the most recent achievements. Coseri S, Biliuta G, Simionescu BC, et al. Carbohydr. Polym. 93(1), 207-15, (2013)


Cellulose nanowhiskers extracted from TEMPO-oxidized jute fibers. Cao X, Ding B, Yu J, et al. Carbohydr. Polym. 90(2), 1075-80, (2012)


Cu-NHC-TEMPO catalyzed aerobic oxidation of primary alcohols to aldehydes. Liu X, Xia Q, Zhang Y, et al. J. Org. Chem. 78(17), 8531-6, (2013)


Enantioselective synthesis of epoxides having a tetrasubstituted trifluoromethylated carbon center: methylhydrazine-induced aerobic epoxidation of β,β-disubstituted enones. Kawai H, Okusu S, Yuan Z, et al. Angew. Chem. Int. Ed. Engl. 52(8), 2221-5, (2013)


The use of cyclic nitroxide radicals as HNO scavengers. Samuni Y, Samuni U, and Goldstein S J. Inorg. Biochem. 118, 155-61, (2013)


Structural characteristics and antioxidant activities of different families of 4-acetamido-TEMPO-oxidised curdlan. Yan JK, Ma HL, Cai PF, et al. Food Chem. 143, 530-5, (2014)


Tuning the reactivity of TEMPO by coordination to a Lewis acid: isolation and reactivity of MCl3(η1-TEMPO) (M = Fe, Al). Scepaniak JJ, Wright AM, Lewis RA, et al. J. Am. Chem. Soc. 134(47), 19350-3, (2012)


Hemigramicidin-TEMPO conjugates: novel mitochondria-targeted anti-oxidants. Fink MP, Macias CA, Xiao J, et al. Biochem. Pharmacol. 74(6), 801-9, (2007)


TEMPO-oxidized nanocellulose participating as crosslinking aid for alginate-based sponges. Lin N, Bruzzese C, and Dufresne A ACS Appl. Mater. Interfaces 4(9), 4948-59, (2012)


Sorption selectivity in natural organic matter studied with nitroxyl paramagnetic relaxation probes. Lattao C, Cao X, Li Y, et al. Environ. Sci. Technol. 46(23), 12814-22, (2012)


Metal-free catalyzed oxidative trimerization of indoles by using TEMPO in air: a biomimetic approach to 2-(1H-indol-3-yl)-2,3'-biindolin-3-ones. Qin WB, Chang Q, Bao YH, et al. Org. Biomol. Chem. 10(44), 8814-21, (2012)


Pulsed electron paramagnetic resonance spectroscopy powered by a free-electron laser. Takahashi S, Brunel LC, Edwards DT, et al. Nature 489(7416), 409-13, (2012)


Green synthesis of silver nanoparticles using 4-acetamido-TEMPO-oxidized curdlan. Yan JK, Cai PF, Cao XQ, et al. Carbohydr. Polym. 97(2), 391-7, (2013)


Biochemical activities of 6-carboxy β-chitin derived from squid pens. Huang J, Chen WW, Hu S, et al. Carbohydr. Polym. 91(1), 191-7, (2013)


Synthesis and biological evaluation of quinazoline and quinoline bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential epidermal growth factor receptor(EGFR) tyrosine kinase inhibitors and EPR bio-probe agents. Siyuan Li et al Eur. J. Med. Chem. 49C, 271-8, (2012)


Hemigramicidin-TEMPO conjugates: novel mitochondria-targeted antioxidants. Fink MP, Macias CA, Xiao J, et al. Crit. Care Med. 35(9 Suppl), S461-7, (2007)


Modification of agarose with carboxylation and grafting dopamine for promotion of its cell-adhesiveness. Su Y, Chu B, Gao Y, et al. Carbohydr. Polym. 92(2), 2245-51, (2013)


Novel spider-web-like nanoporous networks based on jute cellulose nanowhiskers. Cao X, Wang X, Ding B, et al. Carbohydr. Polym. 92(2), 2041-7, (2013)


ERK1/2 activation mediated by the nutlin‑3‑induced mitochondrial translocation of p53. Lee SY, Shin SJ, and Kim HS Int. J. Oncol. 42(3), 1027-35, (2013)


Oxygen insertion of o-quinone under catalytic hydrogenation conditions. Zhang DL, Zhou LY, Quan JM, et al. Org. Lett. 15(6), 1162-5, (2013)


Micro-structural characterisation of homogeneous and layered MFC nano-composites. Chinga-Carrasco G, Averianova N, Gibadullin M, et al. Micron 44, 331-8, (2013)


Preparation of hyaluronan polyaldehyde-a precursor of biopolymer conjugates. Šedová P, Buffa R, Kettou S, et al. Carbohydr. Res. 371, 8-15, (2013)


TEMPO mixed SAMs: electrocatalytic efficiency versus surface coverage. Blanchard PY, Alévêque O, Breton T, et al. Langmuir 28(38), 13741-5, (2012)


Measurement of deoxyinosine adduct: Can it be a reliable tool to assess oxidative or nitrosative DNA damage? Jeong YC, Zhang F, Geter DR, et al. Toxicol. Lett. 214(2), 226-33, (2012)


Transition-metal-free oxidative coupling reactions for the formation of C-C and C-N bonds mediated by TEMPO and its derivatives. Murarka S, Wertz S, and Studer A Chimia 66(6), 413-7, (2012)


Merck 14,9140

Fieser 14,302 / Fieser 16,324 / Fieser 17,332

Aldrich MSDS 1, 1636:A / Corp MSDS 1 (2), 3217:D / FT-IR 1 (2), 908:A / FT-IR 2 (3), 3983:C / IR-Spectra (3), 1420:C / RegBook 1 (2), 2673:J / Sigma FT-IR 1 (2), 901:B / Structure Index 1, 420:C:4

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