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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+%

CAS-Nummer
2564-83-2
Synonyme
2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical

Größe Preis ($) Menge Verfügbarkeit
1g 17,10
5g 44,10
25g 147,60
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

TEMPO, free radical, 98+%

MDL
MFCD00009599
EINECS
219-888-8

Chemische Eigenschaften

Formel
C9H18NO
Molmasse
156.25
Schmelzpunkt
31-40°
Siedepunkt
193° dec.
Flammpunkt
67°(152°F)
Löslichkeit
Soluble in all organic solvents. Insoluble in water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H314-H318

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

Sicherheitshinweise: 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.

Weitere Referenzen

Merck
14,9140
Beilstein
1422418
Gefahrenklasse
8
Verpackungsgruppe
III
Harmonized Tariff Code
2933.39
TSCA
Yes
RTECS
TN8991900

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