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Trifluoromethanesulfonic acid

Description Chemical Properties Preparation Uses Reactions

CAS No.1493-13-6
Chemical Name:Trifluoromethanesulfonic acid
CBNumber:CB7247316
Molecular Formula:CHF3O3S
Formula Weight:150.08
MOL File:1493-13-6.mol

Trifluoromethanesulfonic acid Property

Melting point -40 °C
Boiling point 162 °C (lit.)
Density 1.696 g/mL at 25 °C (lit.)
vapor density 5.2 (vs air)
vapor pressure 8 mm Hg ( 25 °C)
refractive index n20/D 1.327(lit.)
RTECS PB2771000
Flash point None
storage temp. Store below +30°C.
solubility Miscible in H2O
pka -14(at 25℃)
form Fuming Liquid
Specific Gravity 1.696
color slightly brown
PH <1 (H2O)
Viscosity 1.872mm2/s
Water Solubility SOLUBLE
Sensitive Hygroscopic
Merck 14,9676
BRN 1812100
Stability Stable. Incompatible with acids, alkalis, metals.
InChIKey ITMCEJHCFYSIIV-UHFFFAOYSA-N
LogP 0.3 at 25℃
FDA 21 CFR 173.395
Substances Added to Food (formerly EAFUS) TRIFLUOROMETHANE SULFONIC ACID
CAS DataBase Reference 1493-13-6(CAS DataBase Reference)
EWG's Food Scores 2
FDA UNII JE2SY203E8
NIST Chemistry Reference CF3SO3H(1493-13-6)
EPA Substance Registry System Methanesulfonic acid, trifluoro- (1493-13-6)
UNSPSC Code 12352106
NACRES NA.22

Safety

Hazard Codes :C
Risk Statements :21/22-35-10
Safety Statements :26-36/37/39-45
RIDADR :UN 3265 8/PG 2
WGK Germany :2
F :3-10
Hazard Note :Corrosive/Hygroscopic
TSCA :Yes
HazardClass :8
PackingGroup :II
HS Code :29049020
Toxicity :LD50 orally in Rabbit: 1605 mg/kg LD50 dermal Rat > 2000 mg/kg

NFPA 704:

	0
3		1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H290-H302-H314-H335
Precautionary statements P234-P261-P280-P301+P312-P303+P361+P353-P305+P351+P338

Trifluoromethanesulfonic acid Price More Price(14)

Brand: Sigma-Aldrich(India)
Product number: 347817
Product name : Trifluoromethanesulfonic acid
Purity: ReagentPlus?, ≥99%
Packaging: 5G
Price: ₹6910.25
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 8.21166
Product name : Trifluoromethanesulfonic acid
Purity: for synthesis
Packaging: 100ML
Price: ₹6990
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 347817
Product name : Trifluoromethanesulfonic acid
Purity: ReagentPlus?, ≥99%
Packaging: 25G
Price: ₹23399.9
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.21166
Product name : Trifluoromethanesulfonic acid
Purity: for synthesis
Packaging: 1L
Price: ₹45380
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 347817
Product name : Trifluoromethanesulfonic acid
Purity: ReagentPlus?, ≥99%
Packaging: 100G
Price: ₹39056.1
Updated: 2022/06/14
Buy: Buy

Trifluoromethanesulfonic acid Chemical Properties,Usage,Production

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.
Chemical Properties Trifluoromethanesulfonic acid is a hygroscopic, colorless liquid at room temperature. It is soluble in polar solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetonitrile, and dimethyl sulfone. Addition of triflic acid to polar solvents can be dangerously exothermic.
Trifluoromethanesulfonic acid is widely used especially as a catalyst and a precursor in organic chemistry. With an Ka = 8. 0 1014 (pKa ~ -15) mol/kg, HOTf qualifies as a superacid. Triflic acid owes many of its useful properties to its great thermal and chemical stability. Both the acid and its conjugate base CF3SO3-, known as triflate, resist oxidation/reduction reactions, whereas many strong acids are oxidizing, e. g. HClO4 and HNO3. The triflate anion is immune to attack by even strong nucleophiles. Because of its resistance to oxidation and reduction, triflic acid is a very useful and versatile reagent. Further recommending its use, triflic acid does not sulfonate substrates, which can be a problem with sulfuric acid, fluorosulfuric acid, and chlorosulfonic acid. Below is a prototypical sulfonation, which HOTf does not undergo: C6H6 + H2SO4 → C6H5(SO3H) + H2O.
Preparation Yellow-brown liquid. The boiling point is 167~170 ℃.The refractive index is 1.331.The relative density is 1.708.It is the strongest organic acids, easily soluble in water.Use carbon disulfide as raw material, with the reaction of iodine pentafluoride to produce trifluoromethyl disulfide.(CF3S) 2Hg was obtained when reacting with mercury; Then through oxidation of hydrogen oxide, trifluoromethanesulfonic acid is acquired.
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.
Reactions 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.

Catalyst used in the production of cocoa butter substitute from palm oil. This is a very similar reaction to what would be done if one wanted to create polymers using triflic acid in the synthesis. Other Friedel-Crafts type reactions using triflic acid include cracking of alkanes and alkylation of alkenes which are very important to the petroleum industry. These triflic acid derivative catalysts are very effective in isomerizing straight chain or slightly branched hydrocarbons that can increase the octane rating of a particular petroleum based fuel.
Uses Trifluoromethanesulfonic acid acts 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.
Definition ChEBI: Trifluoromethanesulfonic acid is a one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines. It is a one-carbon compound and a perfluoroalkanesulfonic acid. It is a conjugate acid of a triflate.
General Description Trifluoromethanesulfonic acid is a strong organic acid. It can be prepared by reacting bis(trifluoromethylthio)mercury with H₂O₂. On mixing with HNO₃, it affords a nitrating reagent (a nitronium salt). This reagent is useful for the nitration of aromatic compounds. Its dissociation in various organic solvents has been studied.
reaction suitability reaction type: Acid-base reactions
reaction type: Redox Reactions
Safety Profile A corrosive irritant to the skin, eyes, and mucous membranes. A strong acid. Violent reaction with acyl chlorides or aromatic hydrocarbons evolves toxic hydrogen chloride gas. When heated to decomposition it emits toxic fumes of Fand SOx. See also FLUORIDES.