N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamide

• ChemBase ID: 18909
• Molecular Formular: C7H3ClF6N2O4S2
• Molecular Mass: 392.6831392
• Monoisotopic Mass: 391.91269559
• SMILES: n1c(N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)ccc(c1)Cl
• Canonical SMILES: Clc1ccc(nc1)N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F
• InChI: InChI=1S/C7H3ClF6N2O4S2/c8-4-1-2-5(15-3-4)16(21(17,18)6(9,10)11)22(19,20)7(12,13)14/h1-3H
• InChIKey: TUFGVZMNGTYAQD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamide
• IUPAC Traditional name: N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamide
• Synonyms: N-(5-Chloropyridin-2-yl)triflimide; 2-{Bis[(trifluoromethyl)sulphonyl]amino}-5-chloropyridine; 2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine; N,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine; Comins’ Reagent; N-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonimide); 2-[N,N-Bis(trifluoromethanesulfonyl)amino]-5-chloropyridine; 2-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine; 2-[N,N-Bis(trifluoromethanesulfonyl)amino]-5-chloropyridine; N-(5-Chloro-2-pyridyl)triflimide; 2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine; 2-[N,N-双(三氟甲基磺酰)氨基]-5-氯吡啶; N,N-双(三氟甲基磺酰)-5-氯-2-吡啶胺; Comins 试剂; N-(5-氯-2-吡啶基)双(三氟甲烷磺酰亚胺); 2-[N,N-双(三氟甲烷烷磺酰)氨基]-5-氯吡啶

Database IDs

• CAS Number: 145100-51-2
• EC Number: 000-000-0
• MDL Number: MFCD00191833
• Beilstein Number: 5833971
• PubChem SID: 160982216; 24865208
• PubChem CID: 388544

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 4.0276833
• LogD (pH = 7.4): 4.0276833
• Log P: 4.0276833
• Molar Refractivity: 59.7703 cm^3
• Polarizability: 24.491127 Å^3
• Polar Surface Area: 84.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 44-47°C; 45-47 °C(lit.); 45-47°C

Safety Information

• Storage Warning: AIR SENSITIVE, IRRITANT-HARMFUL, KEEP COLD; Harmful/Irritant/Air Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 96%; 98%; 99%
• Empirical Formula (Hill Notation): C7H3ClF6N2O4S2

DETAILS

Sigma Aldrich - 403644

Packaging
1, 5 g in glass bottle
Application
Provides good yields of vinyl triflates from the corresponding ketone enolates or dienolates.1,2,3
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

REFERENCES

• 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).