Trifluoromethanesulfonic acid

Synonym(s):TFMSA;Triflic acid;Triflic acid, TFMS;Trifluoromethanesulfonic acid

CAS NO.：1493-13-6
Empirical Formula: CHF3O3S
Molecular Weight: 150.08
MDL number: MFCD00007514
EINECS: 216-087-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 14:08:57

Trifluoromethanesulfonic acid Structural

What is Trifluoromethanesulfonic acid?

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.

The Uses of Trifluoromethanesulfonic acid

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.

The Uses of Trifluoromethanesulfonic acid

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.

What are the applications of Application

Trifluoromethanesulfonic acid is a strong monoprotic acid

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acid is a one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.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.

Properties of Trifluoromethanesulfonic acid

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 H<sub>2</sub>O
form	Fuming Liquid
appearance	Colorless liquid
pka	-14(at 25℃)
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.
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 for Trifluoromethanesulfonic acid

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H290:Corrosive to Metals H302:Acute toxicity,oral H314:Skin corrosion/irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P234:Keep only in original container. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.