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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%

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

Size Price ($) Quantity Availability
1g 34.50
5g 122.57
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2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, 99%

MDL
MFCD00191833
EINECS
000-000-0

Chemical Properties

Formula
C7H3ClF6N2O4S2
Formula Weight
392.68
Melting point
44-47°
Sensitivity
Moisture Sensitive
Solubility
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.

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: 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.

Other References

Beilstein
5833971
Harmonized Tariff Code
2933.39
TSCA
No

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