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145100-51-2 - 2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, 99% - 2-[N,N-Bis(trifluoromethanesulfonyl)amino]-5-chloropyridine - N-(5-Chloro-2-pyridyl)triflimide - L16929 - Alfa Aesar

L16929 2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, 99%

Codice CAS
145100-51-2
Sinonimi
2-[N,N-Bis(trifluoromethanesulfonyl)amino]-5-chloropyridine
N-(5-Chloro-2-pyridyl)triflimide

Dimensioni Prezzo ($) Quantità Disponibilità
1g 39,70
5g 121,00
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2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, 99%

MDL
MFCD00191833
EINECS
000-000-0

Proprietà chimiche

Formula
C7H3ClF6N2O4S2
Peso formula
392.68
Punto di fusione
44-47°
Sensibilità
Moisture Sensitive
Solubilità
Reacts with water.

Applicazioni

2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates. It is used in the total synthesis of (-)-porantheridine and the trans decahydroquinoline alkaloid (+)-219A. It is also used as a reactant for Suzuki-Miyaura cross coupling, synthesis of nicotinic acetylcholine receptor-selective ligands, enantioselective desymmetrizing palladium catalyzed carbonylation reactions, synthesis of high affinity niacin receptor GPR109A agonists and in preparation of heteroaromatics.

Note

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store under dry inert gas. It is sensitive to moisture.

Letteratura

Haruhiko Fuwa Dr.; Shinya Naito.; Tomomi Goto.; Makoto Sasaki Prof. Dr. Total Synthesis of (+)-Neopeltolide. Angewandte Chemie International Edition. 2008, 47 (25), 4737-4739.

Samantha J. Bamford.; Tim Luker.; W. Nico Speckamp.; Henk Hiemstra. Enantioselective Formal Total Synthesis of Roseophilin. Org. Lett. 2000, 2 (8), 1157-1160.

Highly reactive triflating agent which converts lithium enolates of ketones to vinyl triflates rapidly at low temperatures: Tetrahedron Lett., 33, 6299 (1992). Used in the total synthesis of (-)-porantheridine: J. Am. Chem. Soc. 115, 8851 (1993), and the trans decahydroquinoline alkaloid (+)-219A: J. Org. Chem., 60, 794 (1995).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
5833971
Codice tariffe armonizzato
2933.39
TSCA
No

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