Trifluoromethanesulfonic acid Chemical Properties

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)

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℃

CAS DataBase Reference

1493-13-6(CAS DataBase Reference)

NIST Chemistry Reference

CF3SO3H(1493-13-6)

EPA Substance Registry System

Methanesulfonic acid, trifluoro- (1493-13-6)

Safety Information

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

MSDS

• Language:English Provider:Trifluoromethanesulfonic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Trifluoromethanesulfonic acid Usage And Synthesis

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.

Chemical Properties

Clear very light yellow liquid. Smoke in the air, easy to absorb water to form a hydrate. It is easily soluble in water, releases a lot of heat, and hydrolyzes to generate trifluoromethane (CHF3) and sulfuric acid.

Uses

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.

Uses

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.

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.

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.

Trifluoromethanesulfonic acid(1493-13-6)Related Product Information

• Methyl trifluoromethanesulfonate
• Pefloxacin mesylate
• Citric acid
• (Trifluoromethoxy)benzene
• TRIFLUOROMETHANESULFONYL FLUORIDE
• Stearic acid
• Scandium trifluoromethanesulfonate
• Trifluoromethanesulfonic anhydride
• Cyhalothrin
• Hyaluronic acid
• Methanesulfonic acid
• Trifluoroacetic acid
• Benzotrifluoride
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Levofloxacin Methylate
• Sodium trifluoromethanesulfonate
• Stannous methanesulfonate
• Triflic Acid