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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 번호
2564-83-2
동의어
2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical

사이즈 가격 ($) 수량 재고 여부
1g 19.20
5g 49.00
25g 166.00
장바구니에 추가 대량 견적에 추가 항목 보기

TEMPO, free radical, 98+%

MDL
MFCD00009599
EINECS
219-888-8

화학적 특성

화학식
C9H18NO
화학 식량
156.25
융점
31-40°
비등점
193° dec.
인화점
67°(152°F)
용해도
Soluble in all organic solvents. Insoluble in water.

용도

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.

참고

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

참조 문헌

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 해저드 및 주의 설명서

해저드 설명서 (EU): H314-H318

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

주의 설명서: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

기타 참조

Merck
14,9140
바일슈타인
1422418
위험 등급
8
포장 그룹
III
통합 관세 코드
2933.39
TSCA(독성물질규제법)"
Yes
RTECS(화학물질 독성 등록)
TN8991900

권장

  • A10312

    N-Hydroxysuccinimide, 98+%
  • B24531

    Iodosobenzene diacetate, 98+%
  • 11043

    Ruthenium(III) chloride hydrate, 99.9% (PGM basis), Ru 38% min
  • 33369

    Sodium hypochlorite, 11-15% available chlorine
  • 89892

    Oxone®, monopersulfate

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