Trifluormethansulfonsaeure

Trifluoromethanesulfonic acid

HCID 62406CAS 1493-13-6

Grundinformationen

Standard-SMILES
O=S(=O)(O)C(F)(F)F
InChIKey
ITMCEJHCFYSIIV-UHFFFAOYSA-N
Summenformel
CHF3O3S
Durchschnittliche Molmasse
150,08 g/mol

Überblick

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acid is a one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.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

Namen und Bezeichner

Bevorzugter Name
Trifluoromethanesulfonic acid
IUPAC
trifluoromethanesulfonic acid
Lokaler Name
Trifluormethansulfonsaeure
Englischer Name
Trifluoromethanesulfonic acid
Summenformel
CHF3O3S
Molmasse
150.08

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,3
Polarare Oberfläche (TPSA)
62,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
0
Schwere Atome
8

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 3 Einträge

Other Classes -> Organic Acids

Ionic Liquids -> Fluorinated Ionic Liquids

Ionic Liquids

PFAS · 5 Einträge

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]

Physikochemische Eigenschaften

Schmelzpunkt
-40 °C · -40 °C
Siedepunkt
162 °C · 162 °C (lit.)
Dichte
1.696 g/mL · 1.696 g/mL at 25 °C (lit.)
Dampfdichte
5.2 · 5.2 (vs air)
Dampfdruck
8 mm · 8 mm Hg ( 25 °C)
Brechungsindex
20 · n20/D 1.327(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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]

Gefahrenhinweise

Regulatory Information · 4 Einträge

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 Eintrag

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 Einträge

Met. Corr. 1 (92.8%)

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

Sicherheit und Schutzausrüstung

Protective Action Criteria (PAC) · 3 Einträge

4.8 [mg/m3]

53 [mg/m3]

320 [mg/m3]

Toxikologische Informationen

Health Effects · 1 Eintrag

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 Eintrag

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 Eintrag

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).

Sicherheitsdaten

F
3-10
wgk
2
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
hs_code
29049020
risk_code
21/22-35-10

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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)

Verwendung und Herstellung

Uses · 2 Einträge

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 Einträge

Not Known or Reasonably Ascertainable

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

Anwendungen · 1 Eintrag

VerwendenA 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.

Anbieter50 Anbieter

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INTATRADE GmbH+49 3493/605464 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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.

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