Trifluoromethanesulfonic acid

Base Information

• Chemical Name: Trifluoromethanesulfonic acid
• CAS No.: 1493-13-6
• Deprecated CAS: 132645-03-5,146819-41-2,83936-79-2,410094-25-6,686276-05-1,1071724-18-9,1075754-75-4,2001095-27-6,1071724-18-9,1075754-75-4,146819-41-2,410094-25-6,686276-05-1,83936-79-2
• Molecular Formula: CHF3O3S
• Molecular Weight: 150.078
• Hs Code.: 29049020
• European Community (EC) Number: 216-087-5
• UNII: JE2SY203E8
• DSSTox Substance ID: DTXSID2044397
• Nikkaji Number: J12.301C
• Wikipedia: Triflic_acid,Trifluoromethanesulfonic acid
• Wikidata: Q304850
• Metabolomics Workbench ID: 47395
• ChEMBL ID: CHEMBL1236265
• Mol file: 1493-13-6.mol

Synonyms:Trifluoromethane sulfonic acid;Methanesulfonicacid, trifluoro- (6CI,7CI,8CI,9CI);Fluorad FC 24;Perfluoromethanesulfonicacid;Triflic acid;Trimsylate;

Chemical Property of Trifluoromethanesulfonic acid

Chemical Property:

• Appearance/Colour: Colourless liquid with a pungent odour
• Vapor Pressure: 8 mm Hg ( 25 °C)
• Melting Point: -40 °C
• Refractive Index: n20/D 1.327(lit.)
• Boiling Point: 161.999 °C at 760 mmHg
• PKA: -14(at 25℃)
• Flash Point: None
• PSA: 62.75000
• Density: 1.877 g/cm³
• LogP: 1.47480
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Solubility.: Miscible in H₂O
• Water Solubility.: SOLUBLE
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 149.95984955
• Heavy Atom Count: 8
• Complexity: 158

Purity/Quality:

99.5% min（Titration） ^*data from raw suppliers

Trifluoromethanesulfonic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 21/22-35-10
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: PFAS,Other Classes -> Organic Acids
• Canonical SMILES: C(F)(F)(F)S(=O)(=O)O
• Description: Trifluoromethanesulfonic acid, also known as triflic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is often regarded as one of the strongest acids, and is one of a number of so-called "superacids". it is used in the manufacture of pharmaceuticals, agricultural chemicals and polymers. The anhydrous form is widely used in fine chemical synthesis. It is non-oxidizing, has a high thermal stability, and is resistance to both oxidation and reduction, which makes it one of the more useful compounds in the super acids class. In the pharma industry, it is used to make a number of drug classes, including nucleosides, antibiotics, steroids, proteins and glycosides. Triflic anhydride reacts readily with water and has an unfavorable toxicity profile.
• Uses: It is used for organic synthesis, widely used in pharmaceutical and chemical industries, such as nucleosides, antibiotics, steroids, protein, sugar, vitamins synthesis, silicone rubber modification. Isomerization and alkylation of the catalyst, the preparation of 2, 3-dihydro-2-indanone, tetralone, glycosides in the removal of glycoproteins. As a catalyst in Friedel-Crafts type acylation, alkylation and polymerization reactions; as a solvent for ESR; as a nonaqueous strong acid titrant; with trifluoroacetic acid, q.v., in solid-phase peptide synthesis. One of the strongest available monoprotic acids. Trifluoromethanesulfonic acid acts as a catalyst for esterification reactions and an acidic titrant in nonaqueous acid-base titration. It is useful in protonations due to the presence of conjugate base triflate is non nucleophilic. It serves as a deglycosylation agent for glycoproteins. In addition, it is a precursor and a catalyst in organic chemistry. It reacts with acyl halides to prepare mixed triflate anhydrides, which are strong acylating agents used in Friedel-Crafts reactions. It acts as a key starting material for the preparation of ethers and olefins by reacting with alcohols as well as to prepare trifluoromethanesulfonic anhydride by dehydration reaction.

Technology Process of Trifluoromethanesulfonic acid

There total 98 articles about Trifluoromethanesulfonic acid 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: 75.0%

(E)-1-(4-chlorophenyl)-N-(4-methoxyphenyl)methanimine + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-phenoxyazetidin-2-one

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield: 67.0%

(4-Methoxy-phenyl)-[1-p-tolyl-meth-(Z)-ylidene]-amine (94612-43-8) + C26H22O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-1-(4-Methoxy-phenyl)-3-phenoxy-4-p-tolyl-azetidin-2-one

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield: 61.0%

N-(p-methoxybenzylidene)-p-toluidine (83306-66-5) + C21H20O3P(1+)*CF3O3S(1-) → trifluorormethanesulfonic acid (1493-13-6) + Triphenylphosphine oxide (791-28-6) + (3S,4R)-3-Methoxy-4-(4-methoxy-phenyl)-1-p-tolyl-azetidin-2-one

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

upstream raw materials:

trifluoromethanesulfonic acid ethyl ester

Trifluoromethanesulfonyl fluoride

diethyl ether

methyl trifluoromethanesulfonate

Downstream raw materials:

trifluoromethane sulfonyl chloride

trifluoromethylsulfonic anhydride

phenacyl trifluoromethanesulfonate

pyridinium triflate

Refernces

• 1、 Oudrhiri-Hassani, M.,Brunel, D.,Germain, A. "REACTIVITE DES ESTERS SULFONIQUES ET PYROSULFONIQUES PERFLUORES RFSO3RF ET RFSO3SO3RF. HETEROLYSE DE LA LIAION S-O". . p. 163 - 178. Retrieved 1986.
• 2、 Conte, Lino,Gambaretto, Gian Paolo,Caporiccio, Gerardo,Alessandrini, Fabrizio,Passerini, Stefano. "Perfluoroalkanesulfonylimids and their lithium salts: Synthesis and characterisation of intermediates and target compounds". . p. 243 - 252. Retrieved 2004.
• 3、 Saeva, Franklin D.. "Photoinduced and Thermally Induced Rearrangements in a Thianthrenium Salt System". . p. 37 - 39. Retrieved 1987.
• 4、 Haszeldine, R. N.,Kidd, J. M.. "". . . Retrieved 1954.
• 5、 Rapp et al.. "-". . p. 3642,3644. Retrieved 1950.
• 6、 Kellner,Bliefert. "". . p. 249. Retrieved 1978.
• 7、 -. "METHOD FOR PREPARING OXYSULPHIDE AND FLUORINATED DERIVATIVES IN THE PRESENCE OF AN ORGANIC SOLVENT". Paragraph 0193-0195. . Retrieved 2019/04/05.