2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE

Synonym(s):N,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine;2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine;Comins’ Reagent

CAS NO.：145100-51-2
Empirical Formula: C7H3ClF6N2O4S2
Molecular Weight: 392.68
MDL number: MFCD00191833
EINECS: 629-110-2
SAFETY DATA SHEET (SDS)
Update Date: 2025-07-04 16:04:00

2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE Structural

What is 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE?

Chemical properties

White to pale yellow crystalline solid

The Uses of 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE

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.

The Uses of 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE

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
Preparation of heteroaromatics

Properties of 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE

Melting point:	45-47 °C(lit.)
Boiling point:	77-90°C/0.2mmHg
Density	1.892±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Benzene (Slightly)
form	Solid
pka	-7.71±0.10(Predicted)
color	yellow
Water Solubility	Reacts with water.
Sensitive	Moisture Sensitive
BRN	5833971
Stability:	Moisture Sensitive, Unstable in DMSO Solution
CAS DataBase Reference	145100-51-2(CAS DataBase Reference)

Safety information for 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.