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2564-83-2 - TEMPO, free radical, 98+% - 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical - A12733 - Alfa Aesar

A12733 TEMPO, free radical, 98+%

Número CAS
2564-83-2
Nombre Alternativo
2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical

Tamaño Precio ($) Cantidad Disponibilidad
1g 19,20
5g 49,00
25g 166,00
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TEMPO, free radical, 98+%

MDL
MFCD00009599
EINECS
219-888-8

Propiedades químicas

Fórmula
C9H18NO
Peso molecular
156.25
Punto de fusión
31-40°
Punto de ebullición
193° dec.
Punto de inflamabilidad
67°(152°F)
Solubilidad
Soluble in all organic solvents. Insoluble in water.

Aplicaciones

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.

Notas

Store in a cool place. Incompatible withstrong oxidizing agents and strong acids.

Referencias documentales

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-methyl­imidazolium 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.

Chernick, E. T.; Casillas, R.; Zirzlmeier, J.; Gardner, D. M.; Gruber, M.; Kropp, H.; Meyer, K.; Wasielewski, M. R.; Guldi, D. M.; Tykwinski, R. R. Pentacene Appended to a TEMPO Stable Free Radical: The Effect of Magnetic Exchange Coupling on Photoexcited Pentacene. J. Am. Chem. Soc. 2015, 137 (2), 857-863.

Zhu, X.; Chiba, S. TEMPO-mediated allylic C-H amination with hydrazones. Org. Biomol. Chem. 2014, 12 (26), 4567-4570.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Indicaciones de precaución: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Merck
14,9140
Beilstein
1422418
Clase de peligro
8
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2933.39
TSCA
Yes
RTECS
TN8991900

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