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: 2026-05-27 17:24:25
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. |
Computed Descriptors for 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]-5-CHLOROPYRIDINE
| InChIKey | TUFGVZMNGTYAQD-UHFFFAOYSA-N |
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