Specification
Description
(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl or (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl, commonly known as TEMPO, is a chemical compound with the formula (CH2)3(CMe2)2NO. This heterocyclic compound is a red-orange, sublimable solid. As a stable radical, it has applications in chemistry and biochemistry. TEMPO was discovered by Lebedev and Kazarnowskii in 1960. It is prepared by oxidation of 2,2,6,6-tetramethylpiperidine. TEMPO is widely used as a radical marker, as a structural probe for biological systems in conjunction with electron spin resonance spectroscopy, as a reagent in organic synthesis, and as a mediator in controlled radical polymerization. The stability of this radical is attributed to the resonance provided by non-bonding electrons on the nitrogen atom, which form a 2c3e (half-) bond between nitrogen and oxygen, and hyperconjugative ability. Additional stability arises from the steric protection provided by the four methyl groups adjacent to the nitroxyl group; however, the methyl groups prevent a double bond occurring between either carbon adjacent to nitrogen. The stability of the radical is also indicated by the weakness of the O–H bond in the hydrogenated derivative TEMPO–H. With an O–H bond dissociation energy of about 70kcal/mol, this bond is about 30% weaker than a typical O–H bond.
Synonyms
TEMPO free radical; 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical; 2,2,6,6-Tetramethylpiperidinooxy; 2,2,6,6-Tetramethylpiperidine 1-oxyl
Canonical SMILES
CC1(CCCC(N1[O])(C)C)C
InChI
InChI=1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3
InChI Key
QYTDEUPAUMOIOP-UHFFFAOYSA-N
Solubility
Soluble in all organic solvents. Insoluble in water.
Appearance
Orange crystals or powder
Application
Contact reaction oxidant for iodobenzene diacetyl to oxidize nerol to generate neral. In summary, copper/TEMPO is used for the contact reaction of the 1-alcohol to form an aldehyde.
Storage
Store at 2-8°C, filled with argon
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Hydrogen Bond Acceptor Count
1
Hydrogen Bond Donor Count
0
Monoisotopic Mass
156.138839198
Physical State
Yellow to green powder
Shipping
Can be shipped at room temperature, where not in use may vary.
Stability
Stable. Incompatible with strong acids, strong oxidizing agents. Refrigerate.
Topological Polar Surface Area
4.2 Ų
Undefined Atom Stereocenter Count
0
Undefined Bond Stereocenter Count
0