TEMPO
Synonym(s):2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical;2,2,6,6-Tetramethylpiperidine 1-oxyl;2,2,6,6-Tetramethylpiperidine-1-oxyl (free radical);Tempo
- CAS NO.:2564-83-2
- Empirical Formula: C9H18NO*
- Molecular Weight: 156.25
- MDL number: MFCD00009599
- EINECS: 219-888-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-18 08:51:57
What is TEMPO?
Description
TEMPO, like DABCO, the Molecule of the Week for August 29, 2022, is one of those molecules best known by its acronym. TEMPO’s full name is 2,2,6,6-tetramethyl-1-piperidinyloxy.
TEMPO is also unusual in that it is a stable free radical. Because of its unpaired electron, its color is a bright red-orange, in contrast to similar molecular structures, which do not absorb light in the visible region.
TEMPO was first synthesized in 1959 by USSR chemists O. L. Lebedev and S. N. Kazarnovskii. They oxidized 2,2,6,6-tetramethylpiperidine1 with hydrogen peroxide in the presence of pertungstate ion (WO42–). The authors called the resulting product an “intermediate”; it is not clear whether they realized that it was a free radical. Three years later, another Soviet researcher, A. V. Il’yasov, published data on the effect of solvents on the electron paramagnetic resonance2 (EPR) spectra of some stable free radicals, including TEMPO, so its status had been established by then.
TEMPO has multiple uses in organic chemistry: as a catalyst in oxidation reactions and radical-mediated polymerizations and as an EPR marker or probe in chemical and biochemical systems. In a recent example, Abudureheman Wusiman and co-workers at Xingjiang Normal University (Urumqi, China) used it to promote the mono- and bisimidation of tertiary anilines. The purpose of the reaction was to create a straightforward route to symmetric and unsymmetric N-Mannich bases3 under mild conditions.
1. CAS Reg. No. 768-66-1.
2. Also known as electron spin resonance (ESR).
3. A Mannich base is a β-amino ketone; an N-Mannich base has a nitrogen atom in place of the intermediate carbon atom, e.g., R2NCH2NHC(O)R.
The Uses of TEMPO
TEMPO(2,2,6,6-Tetramethylpiperidinooxy) is a stable radical prepared through the oxidation of 2,2,6,6-tetramethylpiperidine. TEMPO has a wide range of applications including use as a free radical scavenger, a reagent in organic synthe sis and as a structural probe in electron spin resonance spectroscopy. TEMPO can also be used as a mediator in free radical polymerization.
What are the applications of Application
TEMPO is a catalyst employed in the oxidation of primary alcohols to aldehydes with NaOCl
Properties of TEMPO
Melting point: | 36-38 °C(lit.) |
Boiling point: | 193°C |
Density | 1 g/cm3 |
Flash point: | 154 °F |
storage temp. | Store below +30°C. |
solubility | 9.7g/l |
form | Powder |
appearance | dark red to red-orange crystals or powder |
appearance | Red-orange solids |
color | Yellow to green |
Water Solubility | Soluble in all organic solvents. Insoluble in water. |
Safety information for TEMPO
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 |
GHS Hazard Statements |
H314:Skin corrosion/irritation H412:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for TEMPO
InChIKey | RVWUHFFPEOKYLB-UHFFFAOYSA-N |
Abamectin manufacturer
SAGAR LIFE SCIENCES PVT LTD
SURVIVAL TECHNOLOGIES LIMITED
Arown Pharma
JSK Chemicals
Covalent Incorporation
Sintilla Medcoms Pvt Ltd
THINQ Pharma CRO Ltd
New Products
3-N-BOC-(S)-AMINO BUTYRONITRILE 4-Piperidinopiperidine 2-Methyl-4-nitrobenzoic acid 2-(4-bromophenyl)-2-methylpropanoic acid 4-Acetyl-2-methylbenzoicacid Acetyl-meldrum's acid Ethyl-4-Pyrazole carboxylate 2,6 Di acetylpyridine 2,6-Pyridinedimethanol 5,7-Dichloro-3H-Imidazo[4,5-B]Pyridine 5-Bromo-2-Methoxy-4-Methyl-3-Nitropyridine 2-Fluoro-5-Iodopyridine 2-Fluoro-5-Methylpyridine 2-Chloro-3-Bromo-5-Amiopyridine METHYL-4-(BUTYRYLAMINO)3-METHYL-5-NITROBENZOATE TRANS-CYCLOBUTANE-1,2- DICARBOXYLIC ACID 5-Nitro indazole R-(-)-5-(2-AMINO-PROPYL)-2-METHOXY-BENZENESULFONAMIDE 1,3-cyclohexanedione 4-Aminophenaethylalchol (S)-(+)-4-BENZYL-2-OXAZOLIDINONE 3-NITRO-5-ACETYL IMINODIBENZYL 4-FLUORO PHENYL MAGNESIUM BROMIDE 1.0 M IN THF 1-HYDROXY-4-METHYL6-(2,4,4-TRI METHYL PHENYL)-2-PYRIDONE MONO ETHANOL AMINE(PIROCTONE OLAMINE)Related products of tetrahydrofuran
You may like
-
2564-83-2 98%View Details
2564-83-2 -
TEMPO FREE RADICAL 99%View Details
2564-83-2 -
TEMPO, FREE RADICAL 2564-83-2 98%View Details
2564-83-2 -
2564-83-2 2,2,6,6-Tetramethylpiperidinyloxy (TEMPO Free Radical) 99%View Details
2564-83-2 -
2564-83-2 99%View Details
2564-83-2 -
2,2,6,6-Tetramethylpiperidinyloxy, 98% 99%View Details
2564-83-2 -
2,2,6,6-Tetramethylpiperidinyloxy 98%View Details
-
2564-83-2 2,2,6,6-Tetramethylpiperidine 1-Oxyl 99%View Details
2564-83-2