2-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine

Base Information

• Chemical Name: 2-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine
• CAS No.: 145100-51-2
• Molecular Formula: C7H3ClF6N2O4S2
• Molecular Weight: 392.687
• Hs Code.: 29350090
• European Community (EC) Number: 629-110-2
• NSC Number: 683533
• UNII: WS933U9U66
• DSSTox Substance ID: DTXSID40327763
• Nikkaji Number: J782.013E
• Wikipedia: Comins%27_reagent,Comins'_reagent
• Wikidata: Q5151993
• Mol file: 145100-51-2.mol

Synonyms:145100-51-2;2-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine;2-[N,N-Bis(trifluoromethanesulfonyl)amino]-5-chloropyridine;N-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonimide);Comins' Reagent;N-(5-Chloro-2-pyridyl)triflimide;N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide;2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine;Comins Triflating Reagent;NSC683533;NSC-683533;WS933U9U66;MFCD00191833;N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide;n-(5-chloropyridin-2-yl)-1,1,1-trifluoro-n-[(trifluoromethyl)sulfonyl]methanesulfonamide;N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-trifluoromethanesulfonylmethanesulfonamide;N,N-Bis(trifluoromesyl)-5-chloropyridine-2-amine;N,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridinamine;1-(N,N-Bis(trifluoromethylsulfonyl)amino)-5-chloropyridine;2-(N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine;2-[N,N-Bis(trifluromethanesulfonyl)amino]-5-chloropyridine;2-(N,N-Bis(trifluoromethylsulphonyl)amino)-5-chloropyridine;N-(5-Chloro-2-pyridyl)-N-(trifluoromethanesulfonyl)trifluoromethanesulfonamide;Methanesulfonamide, N-(5-chloro-2-pyridinyl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]-;N-(5-Chloro-2-pyridinyl)-1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide;2-(n,n-bis(trifluoromethylsulfonyl)amino)-5-chloropyridine;2-(n,n-bis(trifluromethanesulfonyl)amino)-5-chloropyridine;Comins reagent;SCHEMBL69571;UNII-WS933U9U66;N-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonyl)imide;DTXSID40327763;BCP15384;n-(5-chloro-2-pyridyl) triflimide;BBL100395;STL554189;n-(5-chloropyridin-2-yl)-triflimide;AKOS005254564;AC-5150;CS-W009001;MB00872;N-(5-chloro-2-pyridyl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide;AS-18113;SY025226;AM20050816;FT-0610888;EN300-7394471;A808319;bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine;Q5151993;W-205618;N,N-Bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine;[N,N'-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine;2-[N,N'-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine;2-[n,n-bis(trifluormethyl-sulfonyl)amino]-5-chloropyridine;2-[N,N-bis(trifluoromethylsulfonyl) amino]-5-chloropyridine;2-[N,N-bis(trifluoromethylsulfonyl)amino ]-5-chloropyridine;2-[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloro-pyridine;2-[N,N-bis(trifluoromethylsulfonyl)amino]5-chloropyridine;2-[N,N-Bis(trifluoromethylsulphonyl)amino]-5chloropyridine;2[N,N- bis(trifluoromethylsulfonyl)amino]-5-chloropyridine;2[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine;N-(5-Chloro-2-pyridyl)bis(trifluoromethanesulfonimide), 96%;2-[N,N-BIS(TRIFLUOROMETHANESULPHONYL)AMINO]-5-CHLOROPYRIDINE;N-(5-Chloropyridin-2-yl)-1,1,1-trifluoro-N-(trifluoromethanesulfonyl)methanesulfonamide;N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl) sulfonyl]methanesulfonamide;N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]-methanesulfonamide;2-[N,N-bis(trifluoroMethylsulphony)aMino]-5-chloropyridine

Chemical Property of 2-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine

Chemical Property:

• Appearance/Colour: White to pale yellow crystalline solid
• Vapor Pressure: 13.9mmHg at 25°C
• Melting Point: 45-47 °C(lit.)
• Refractive Index: 1.379
• Boiling Point: 358.316 °C at 760 mmHg
• PKA: -7.71±0.10(Predicted)
• Flash Point: 170.504 °C
• PSA: 101.17000
• Density: 1.893 g/c³
• LogP: 4.40220
• Storage Temp.: Keep Cold
• Sensitive.: Moisture Sensitive
• Solubility.: Benzene (Slightly)
• Water Solubility.: Reacts with water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 391.9126956
• Heavy Atom Count: 22
• Complexity: 561

Purity/Quality:

99% ^*data from raw suppliers

2-[N,N-Bis(trifluoromethylsulfonyl)amino]-5-chloropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=NC=C1Cl)N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F
• Uses: 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. 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

Technology Process of 2-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine

There total 1 articles about 2-[N,N-Bis(Trifluoromethylsulphonyl)amino]-5-chloropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

5-chloro-2-pyridylamine (1072-98-6) + trifluoromethylsulfonic anhydride (358-23-6) → N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2)

Guidance literature:

With pyridine; In dichloromethane; 1.) -78 deg C, 1 h 2.) rt, 12 h;

DOI:10.1016/S0040-4039(00)60957-7

Reference yield: 98.0%

methyl (S)-2-hydroxy-2-(3-hydroxyphenyl)-2-phenylacetic acid + N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) → methyl (S)-2-hydroxy-2-phenyl-2-(3-(((trifluoromethyl)sulfonyl)oxy)phenyl)acetate

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 18h;

Reference yield: 96.0%

(R)-tert-butyl-(2-(8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)(4-hydroxyphenethyl)carbamate + N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) → (R)-4-(2-((2-(8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)(tert-butoxycarbonyl)amino)ethyl)phenyl trifluoromethanesulfonate

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

upstream raw materials:

5-chloro-2-pyridylamine

trifluoromethylsulfonic anhydride

Downstream raw materials:

Trifluoro-methanesulfonic acid 3,3,5-trimethyl-cyclohexa-1,5-dienyl ester

5,5-diphenyl-2-{[(trifluoromethyl)sulfonyl]oxy}-1,3-cyclohexadiene

1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene

(2R,6S)-2,6-Diphenyl-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester

Refernces

• 1、 Lindstroem,Ripa,Hallberg. "Synthesis of two conformationally constrained analogues of the minor tobacco alkaloid anabasine.". . p. 2291 - 2293. Retrieved 2007/10/03.
• 2、 Comins, Daniel L.,Dehghani, Ali. "Pyridine-Derived Triflating Reagents: An Improved Preparation of Vinyl Triflates from Metallo Enolates.". . p. 6299 - 6302. Retrieved 2007/10/02.