Trifluoromethanesulfonic anhydride

Base Information

• Chemical Name: Trifluoromethanesulfonic anhydride
• CAS No.: 358-23-6
• Deprecated CAS: 93916-16-6
• Molecular Formula: C2F6O5S2
• Molecular Weight: 282.141
• Hs Code.: 29049020
• European Community (EC) Number: 206-616-8
• UNII: 8W034LHG1U
• DSSTox Substance ID: DTXSID501014629
• Nikkaji Number: J39F
• Wikipedia: Trifluoromethanesulfonic_anhydride
• Wikidata: Q6128335
• Metabolomics Workbench ID: 57027
• Mol file: 358-23-6.mol

Synonyms:Methanesulfonicacid, trifluoro-, anhydride (6CI,7CI,8CI,9CI);Perfluoromethanesulfonicanhydride;Tirflic anhydride;Triflate anhydride;Triflic acid anhydride;Triflic anhydride;Trifluoromethanesulfonic acid anhydride;Trifluoromethylsulfonic acid anhydride;Trifluoromethylsulfonic anhydride;

Chemical Property of Trifluoromethanesulfonic anhydride

Chemical Property:

• Appearance/Colour: clear colorless to light brown liquid
• Vapor Pressure: 8 mm Hg ( 20 °C)
• Melting Point: -80 °C
• Refractive Index: n20/D 1.321(lit.)
• Boiling Point: 82.6 °C at 760 mmHg
• Flash Point: 81-83°C
• PSA: 94.27000
• Density: 1.976 g/cm³
• LogP: 2.86380
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with dichloromethane. Immiscible with hydrocarbons.
• Water Solubility.: reacts violently with water
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 2
• Exact Mass: 281.90913442
• Heavy Atom Count: 15
• Complexity: 370

Purity/Quality:

98% ^*data from raw suppliers

Trifluoromethanesulfonic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-21/22-34-35-22-40
• Safety Statements: 26-36/37/39-43-45-8

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Acid Anhydrides, Other
• Canonical SMILES: C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
• Uses: Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group. Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.

Technology Process of Trifluoromethanesulfonic anhydride

There total 44 articles about Trifluoromethanesulfonic anhydride 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: 92.0%

chloroform (67-66-3,8013-54-5) + Chlorine(I) trifluoromethanesulfonate (65597-24-2) → trifluorormethanesulfonic acid (1493-13-6) + trifluoromethylsulfonic anhydride (358-23-6)

Guidance literature:

at 22 ℃; for 1h;

DOI:10.1016/S0022-1139(00)85216-1

Reference yield: 0.5%

silver trifluoromethanesulfonate (2923-28-6) → iodotrifluoromethane (2314-97-8,263005-66-9) + trifluoromethylsulfonic anhydride (358-23-6)

Guidance literature:

at higher temp.;

Reference yield:

trifluorormethanesulfonic acid (1493-13-6) + acetonitrile (75-05-8,26809-02-9) → 2,6-dimethylpyrone (1004-36-0) + 3-acetyl-2,6-dimethyl-4H-pyran-4-one (7521-38-2) + C2H7N2(1+) (31111-45-2) + trifluoromethylsulfonic anhydride (358-23-6) + acetacidium (17104-45-9,18639-92-4) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + oxoethylium (15762-07-9) + N-acetylacetamidine (1361550-85-7,5699-42-3) + 2,4-dimethyl-1,6-dihydro-6-pyrimidone (6622-92-0)

Guidance literature:

In dichloromethane-d2; at 74 ℃; Cooling;

DOI:10.1039/c2ob06841a

upstream raw materials:

trifluorormethanesulfonic acid

chloroform

Chlorine(I) trifluoromethanesulfonate

Dichlorodifluoromethane

Downstream raw materials:

isobutyl triflate

Trimethylsilylmethyl trifluoromethanesulfonate

4-Benzoyltrifluoromethanesulfonanilid

N-(3-chloro-2-methylphenyl)-1,1,1-trifluoromethanesulfonamide

Refernces

• 1、 Flores, Daniel M.,Schmidt, Valerie A.. "Intermolecular 2 + 2 Carbonyl-Olefin Photocycloadditions Enabled by Cu(I)-Norbornene MLCT". . p. 8741 - 8745. Retrieved 2019.
• 2、 Roberts,R.M.G.. "-". . p. 1183 - 1190. Retrieved 1976.
• 3、 -. "A method of manufacturing a sulfonic acid anhydride Fluoroalkanoic (by machine translation)". Paragraph 0059-0061. . Retrieved 2017/02/23.