Pyridinium trifluoromethanesulfonate

Base Information

• Chemical Name: Pyridinium trifluoromethanesulfonate
• CAS No.: 52193-54-1
• Molecular Formula: CF₃O₃S*C₅H₆N
• Molecular Weight: 229.18
• Hs Code.: 2933399090
• European Community (EC) Number: 626-480-7
• DSSTox Substance ID: DTXSID50370543
• Mol file: 52193-54-1.mol

Synonyms:Pyridinium trifluoromethanesulfonate;52193-54-1;Pyridinium triflate;pyridin-1-ium trifluoromethanesulfonate;pyridin-1-ium;trifluoromethanesulfonate;PYRIDINIUMTRIFLUOROMETHANESULFONATE;C6H6F3NO3S;SCHEMBL318231;DTXSID50370543;pyridinium trifluoromethanesulphonate;AKOS015852954;CS-0099020;FT-0700859;P1627;D92140

Chemical Property of Pyridinium trifluoromethanesulfonate

Chemical Property:

• Vapor Pressure: 1.14mmHg at 25°C
• Melting Point: 221-223 °C(lit.)
• Boiling Point: 162°C at 760 mmHg
• Flash Point: 129.1°C
• PSA: 75.64000
• LogP: 2.55640
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: It is miscible with water, soluble in polar solvents.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 229.00204871
• Heavy Atom Count: 14
• Complexity: 176

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pyridinium trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=[NH+]C=C1.C(F)(F)(F)S(=O)(=O)[O-]
• Uses: Catalytic amounts of pyridinium triflate in conjunction with silylbenzamide is a versatile reagent for the silylation of alcohols. Pyridinium trifluoromethanesulfonate, esters are used as a catalyst for the reactions of: condensation of alcohols and carboxylic acids, reaction of aromatic compounds with sulfonyl chlorides, cracking of alkanes, alkylation of alkenes, isomerisation of alkanes and trans-alkylation of aromatics, trans-bromination and other Friedel-Crafts reactions.

Technology Process of Pyridinium trifluoromethanesulfonate

There total 10 articles about Pyridinium trifluoromethanesulfonate 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: 95.0%

pyridine (110-86-1) + DOTf (66178-41-4) → duetero-pyridinium triflate (52193-54-1)

Guidance literature:

In dichloromethane; at 22 - 26 ℃; for 0.75h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201305711

Reference yield:

pyridine (110-86-1) + trifluoromethylsulfonic anhydride (358-23-6) → pyridinium triflate (21179-04-4,52193-54-1)

Guidance literature:

With 3-Butyn-1-ol; In tetrachloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1002/chem.200801904

Reference yield:

{(η5-Cp)iron(carbonyl)2CH2C(OH)(carbonyl)2iron(η-Cp)}(TfO) (111582-14-0) → {(η5-C5H5)Fe(CO)2}CH2(CO){(η5-C5H5)Fe(CO)2}, η1-(C)-enolate complex + pyridinium triflate (21179-04-4,52193-54-1)

Guidance literature:

With pyridine; In chloroform-d1; (FpCH2C(OH)Fp)(TfO), pyridine and CDCl3 are sealed in an NMR tube, dissolution by ultrasonification results in white solid ppt.; Centrifugation, (1)H NMR, IR.;

upstream raw materials:

pyridine

trifluorormethanesulfonic acid

methyl-phenyl-thioether

N-fluoropyridinium triflate

Downstream raw materials:

3-oxo-3-phenylprop-1-en-2-yl acetate

Refernces

• 1、 Hervé, Alexandre,Bouzidi, Yamina,Berthet, Jean-Claude,Belkhiri, Lotfi,Thuéry, Pierre,Boucekkine, Abdou,Ephritikhine, Michel. "UIII-CN versus UIV-NC coordination in tris(silylamide) complexes". . p. 2474 - 2490. Retrieved 2015/03/18.
• 2、 Marwitz, Adam J. V.,Jenkins, Jesse T.,Zakharov, Lev N.,Liu, Shih-Yuan. "1,2-azaborine cations". supporting information; experimental part. p. 7444 - 7447. Retrieved 2010/11/20.