Search Thermo Fisher Scientific
Element Search
Structure Search
Thermo Scientific Chemicals
TEMPO, free radical, 98+%, Thermo Scientific Chemicals
Have Questions?
Change view
Catalog number A12733.03
also known as A12733-03
Price (USD)/ Each
28.10
-
Quantity:
1 g
Price (USD)/ Each
28.10
TEMPO, free radical, 98+%, Thermo Scientific Chemicals
Catalog numberA12733.03
Price (USD)/ Each
28.10
-
Chemical Identifiers
CAS2564-83-2
IUPAC Name(2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl
Molecular FormulaC9H18NO
InChI KeyQYTDEUPAUMOIOP-UHFFFAOYSA-N
SMILESCC1(C)CCCC(C)(C)N1[O]
View more
Specifications
Specification Sheet
Specification SheetAppearance (Color)Orange-red to red to dark red
FormCrystalline powder or powder or crystals or fused solid and/or chunks
Assay (GC)≥98.0%
Identification (FTIR)Conforms
Melting Point (clear melt)31-40°C
TEMPO is used as a catalyst in organic synthesis and for the oxidation of primary alcohols to aldehydes. It finds use in the chemical industry for conversion of bisnoralcohol (a steroid) to bisnoraldehyde. It acts as a free radical scavenger, as a mediator in controlled radical polymerization and as a structural probe in electron spin resonance spectroscopy. Further, it is involved in the preparation of (S)-(+)-2-methylbutanal from (S)-(-)-2-methyl-1-butanol.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
TEMPO is used as a catalyst in organic synthesis and for the oxidation of primary alcohols to aldehydes. It finds use in the chemical industry for conversion of bisnoralcohol (a steroid) to bisnoraldehyde. It acts as a free radical scavenger, as a mediator in controlled radical polymerization and as a structural probe in electron spin resonance spectroscopy. Further, it is involved in the preparation of (S)-(+)-2-methylbutanal from (S)-(-)-2-methyl-1-butanol.
Solubility
Soluble in all organic solvents. Insoluble in water.
Notes
Store in a cool place. Incompatible withstrong oxidizing agents and strong acids.
TEMPO is used as a catalyst in organic synthesis and for the oxidation of primary alcohols to aldehydes. It finds use in the chemical industry for conversion of bisnoralcohol (a steroid) to bisnoraldehyde. It acts as a free radical scavenger, as a mediator in controlled radical polymerization and as a structural probe in electron spin resonance spectroscopy. Further, it is involved in the preparation of (S)-(+)-2-methylbutanal from (S)-(-)-2-methyl-1-butanol.
Solubility
Soluble in all organic solvents. Insoluble in water.
Notes
Store in a cool place. Incompatible withstrong oxidizing agents and strong acids.
RUO – Research Use Only
General References:
- For brief features on TEMPO and related reagents, see: Synlett, 563 (2001); 1757 (2003); 657 (2006). For reviews on nitroxide radicals, see: Synthesis, 190, 401 (1971); Chem. Rev., 78, 37 (1978); J. Sci. Ind. Res., 54, 623 (1995).
- In the presence of a catalytic amount of KBr, catalyzes the selective oxidation of primary and secondary alcohols to aldehydes and ketones by buffered NaOCl: J. Org. Chem., 50, 4888 (1985); 52, 2559 (1987); Org. Synth. Coll., 8, 367 (1993). High yields of aldehydes can also be obtained under mild, phase-transfer conditions with Oxone™: Org. Lett., 2, 1173 (2000). In the presence of CuCl, aerobic oxidation of alcohols to aldehydes and ketones has been accomplished in the ionic liquid 1-n-Butyl-3-methyl imidazolium hexafluorophosphate, L19086: Org. Lett., 4, 1507 (2002). With NaOCl, ɑ-amino or ɑ-alkoxy alcohols have also been oxidized to the aldehydes: Tetrahedron Lett., 33, 5029 (1992). The use of I2 as cooxidant is useful for sensitive substrates: Org. Lett., 5, 235 (2003).
- The addition of quaternary salts to the reaction mixture permits further oxidation of aldehydes to acids. Selective oxidation of a primary OH to an aldehyde can be achieved in the presence of a secondary OH: J. Org. Chem., 54, 2970 (1989); Tetrahedron Lett., 31, 2177 (1990). The oxidation can also be performed using NCS under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996), with Iodosobenzene diacetate, B24531: J. Org. Chem., 62, 6974 (1997), or Trichloroisocyanuric acid, B23906: Org. Lett., 3, 3041 (2001).
- For a review of the use of stable nitroxyl radicals for the oxidation of primary and secondary alcohols, see: Synthesis, 1153 (1996).
- Cf also 4-Hydroxy-TEMPO, A12497, and 4-Acetamido-TEMPO, B23456.