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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%

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

Dimensions Prix ($) Quantité Disponibilité
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

Propriétés chimiques

Formule
C7H3ClF6N2O4S2
Poids formulaire
392.68
Point de fusion
44-47°
Sensibilité
Moisture Sensitive
Solubilité
Reacts with water.

Applications

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.

Notes

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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

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

Mentions de prudence: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
5833971
Code tarifaire harmonisé
2933.39
TSCA
No

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