Trifluoromethanesulfonic acid

HCID 62406

Basic information

CAS
1493-13-6
Standard SMILES
O=S(=O)(O)C(F)(F)F
InChIKey
ITMCEJHCFYSIIV-UHFFFAOYSA-N
Molecular formula
CHF3O3S
Average molar mass
150.08 g/mol

Overview

Triflic acid is a one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.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 perfluoroalkanesulfonic acid and a one-carbon compound. It is a conjugate acid of a triflate.

Names & identifiers

Preferred name
Trifluoromethanesulfonic acid
IUPAC
trifluoromethanesulfonic acid
English name
Trifluoromethanesulfonic acid
Molecular formula
CHF3O3S
Molecular weight
150.08

Names & synonyms

Trifluoromethanesulfonic acid1493-13-6Triflic acidPerfluoromethanesulfonic acidTrifluoromethanesulphonic acidtfmsaTrifluoromethane sulfonic acidTfOHDTXSID2044397HOTfJE2SY203E8Trifluormethansulfonsaeure
Show more names
Triflatetrifluorormethanesulfonic acidTFMStrifluoromethanesulfonictriflic
DTXCID0024397CHEBI:485111,1,1-trifluoromethanesulfonic acidAgOTf cpdCu(OTf)2Eu(OTf)3TFMSA cpdRefChem:191595

Database identifiers

CAS
1493-13-6
PubChem CID
62406
DTXSID
DTXSID2044397
ChEMBL
CHEMBL1236265
ChEBI
CHEBI:48511
UNII
JE2SY203E8
EC Number
216-087-5
Nikkaji
J12.301C

Properties

Computed structural properties

XLogP
0.3
Topological polar surface area
62.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical Classes · 3 items

Other Classes -> Organic Acids

Ionic Liquids -> Fluorinated Ionic Liquids

Ionic Liquids

PFAS · 5 items

PFAS -> Perfluorosulfonic acids

PFAS -> Ultra Short Chain PFsulfonic acids

PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008

PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds

PFAS -> PFAS with analytical method available

SpringerMaterials PropertiesSchoenflies notation
Food AdditivesUse unspecified -> FDA Substance added to food
Density1.696 @25 °C
Boiling Point162 °C @760 [mm Hg]

Physicochemical properties

Melting point
-40 °C · -40 °C
Boiling point
162 °C · 162 °C (lit.)
Density
1.696 g/mL · 1.696 g/mL at 25 °C (lit.)
vapor density
5.2 · 5.2 (vs air)
vapor pressure
8 mm · 8 mm Hg ( 25 °C)
refractive index
20 · n20/D 1.327(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H290 (92.8%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P330, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2365 reports by companies from 34 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Hazard information

Regulatory Information · 4 items

Chemical: Methanesulfonic acid, trifluoro-

Methanesulfonic acid, 1,1,1-trifluoro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanesulfonic acid, 1,1,1-trifluoro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 03-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5311

Trifluoromethanesulphonic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Highly corrosive to skin; [Quick CPC] One of the strongest acids known. May cause burns; [Merck Index] Oral LD50 (rat) is between 500 and 2,000 mg/kg; An acute dermal toxicity study of rats at 2,000 mg/kg produced extensive and severe local skin effects considered to be life threatening; 50 mg/kg doses were tolerated and showed no significant adverse effects at necropsy; No evidence of skin sensitization in guinea pigs; No evidence of mutagenicity; [EPA TSCA] Causes burns; Inhalation of high concentration can cause chemical pneumonitis; [Alfa Aesar MSDS]

Hazard Classes and Categories · 2 items

Met. Corr. 1 (92.8%)

Serious eye damage/eye irritation - Category 2A-2B

Safety & protection

Protective Action Criteria (PAC) · 3 items

4.8 [mg/m3]

53 [mg/m3]

320 [mg/m3]

Toxicology

Health Effects · 1 item

Silver itself is not toxic to humans, but most silver salts are. In large doses, silver and compounds containing it can be absorbed into the circulatory system and become deposited in various body tissues, leading to argyria, which results in a blue-grayish pigmentation of the skin, eyes, and mucous membranes. Argyria is rare, and although, so far as known, this condition does not otherwise harm a person's health, it is disfiguring and usually permanent. Mild forms of argyria are sometimes mistaken for cyanosis. (L809)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L808) ; inhalation (L808) ; dermal (L808)
Toxicity Summary · 1 item

Metallic silver is oxidized and may deposit in the tissues, causing arygria. The silver ion is known to inhibit glutathione peroxidase and NA+,K+-ATPase activity, disrupting selenium-catalyzed sulfhydryl oxidation-reduction reactions and intracellular ion concentrations, respectively. Silver nanoparticles are believed to disrupt the mitochondrial respiratory chain, causing oxidative stress, reduced ATP synthesis, and DNA damage. (L808, A243, A244, A245, A246)

Signs and Symptoms · 1 item

Exposure to high levels of silver for a long period of time may result in a condition called arygria, a blue-gray discoloration of the skin and other body tissues. Argyria is a permanent effect but does not appear to be harmful to health. Exposure to high levels of silver in the air has resulted in breathing problems, lung and throat irritation, and stomach pains. Skin contact with silver can cause mild allergic reactions such as rash, swelling, and inflammation in some people. (L808)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

F
3-10
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
hs_code
29049020

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Silver and its compounds can be absorbed via inhalation, while silver compounds can also be absorbed orally and dermally. It distributes throughout the body in the blood, particularily to the liver. Insoluble silver salts are transformed into soluble silver sulfide albuminates, bind to amino or carboxyl groups in RNA, DNA, and proteins, or are reduced to metallic silver by ascorbic acid or catecholamines. Metallic silver is oxidized and may deposit in the tissues, causing arygria. Silver is eliminated primarily in the faeces. (L808)

Uses & manufacturing

Uses · 2 items

Used as a catalyst, solvent for ESR, acid titrant, and with trifluoroacetic acid in peptide synthesis; [Merck Index]

Silver trifluoromethanesulfonate is used in inorganic and organometallic chemistry to replace halide anions or ligands. (L833)

U.S. Production2023: 26,136 lb
Industry UsesNot Known or Reasonably Ascertainable
Use ClassificationPFAS -> Ultra Short Chain PFsulfonic acids
General Manufacturing Information · 2 items

Not Known or Reasonably Ascertainable

Methanesulfonic acid, 1,1,1-trifluoro-: ACTIVE

Applications · 5 items

DescriptionTrifluoromethanesulfonic 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.

UsesIt 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.

UsesA cost-effective process for synthesizing daidzein was developed by Hai Cao and colleagues[1]. A two-step synthesis of daidzein (Friedel–Crafts acylation and [5+1] cyclization) was developed via the employment of trifluoromethanesulfonic acid (TfOH) as an effective promoting reagent. Due to the facilitating effect of TfOH, the Friedel–Crafts acylation was completed within 10 min at 90 °C and the [5+1] cyclization was completed within 180 min at 25 °C.

UsesTrifluoromethanesulfonic 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.

General DescriptionTrifluoromethanesulfonic 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.

Preparation methods · 1 item

PreparationYellow-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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
中船(邯郸)派瑞特种气体股份有限公司021-53930372 13917175395
INTATRADE GmbH+49 3493/605464 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

1,687 records

Compound notes

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