This article about an organic compound is a stub. Trifluormethansulfonsäure 3-fluor-4''-propyl-1,1':4',1''-ter phenyl-4-ylester. This compound is however unstable even at low temperatures. The date of the last update corresponds to the publication date of the InfoCard and not necessarily to the date in which the update occurred in the source data. Für die Triflatgruppe wird in Fachpublikationen zumeist die Abkürzung „OTf“ verwendet; die Abkürzung „Tf“ steht für die Trifluormethansulfonylgruppe –SO2CF3, auch Triflylgruppe genannt. [61], In asymmetric trifluoromethylation the trifluoromethyl group is added to the substrate in an enantioselective way. Das Triflatanion widersteht selbst starken Nucleophilen. Wie oben bereits erwähnt, können sie direkt aus der Reaktion der Säure mit Metallhydroxiden oder Metallcarbonaten in wässriger Lösung gewonnen werden. Grund dafür ist extreme Stabilität des Triflatanions, zum einen durch mesomere Verteilung der negativen Ladung über die drei Sauerstoffatome und den Schwefel: Zusätzlich wird diese Ladung durch den kräftigen elektronenziehenden Effekt (hohe Elektronegativität der drei Fluoratome) der Trifluormethylgruppe stabilisiert. in Friedel–Crafts reactions. Study with Quizlet and memorize flashcards containing terms like 25, 9,0, 9,2 and more. The CAS number is the substance numerical identifier assigned by the Chemical Abstracts Service, a division of the American Chemical Society, to substances registered in the CAS registry database. Produktname : Trifluormethansulfonsäure zur Synthese Produktnummer : 8.21166 Artikelnummer : 821166 Marke : Millipore REACH Nr. PubChem Substance ID: 24861529 NACRES: NA.22 Pricing and availability is not currently available. Nitromethan ist auf eine Dissoziation in Alkylsulfenylium-Ionen, die als . The reagent has been applied with heterocyclic substrates[29], Umemoto reagents are (trifluoromethyl)dibenzoheterocyclic salts, such as 5-(trifluoromethyl)dibenzothiophenium triflate and 5-(trifluoromethyl)dibenzothiophenium tetrafluoroborate. Dibutylboron trifluoromethanesulfonate (also called dibutylboron triflate or DBBT) is a reagent in organic chemistry. A substance identified primarily by an EC or list number may be linked with more than one CAS number, or with CAS numbers that have been deleted. Es ist nützlich bei Protonierungen aufgrund des Vorhandenseins der konjugierten Base. Reference substance name: Trifluoromethanesulphonic acid EC Number: 216-087-5 EC Name: Trifluoromethanesulphonic acid . trifluoromethanesulfonic acid trichlormethylester, 2,6-dimethylbenzoic trifluoromethanesulfonic anhydride, 2,4,6-Trimethylbenzoesaeure-trifluomethansulfonsaeure-anhydrid, 4-Methoxy-2,6-dimethylbenzoesaeure-trifluormethansulfonsaeure-anhydrid, 2,6-Dimethyl-4-nitrobenzoesaeure-trifluormethansulfonsaeure-anhydrid, 4-Chlor-2,6-dimethylbenzoesaeure-trifluormethansulfonsaeure-anhydrid, Enter 15 to 2000 letters.Word count: 0 letters, What can I do for you? (cs) Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF 3 SO 3 H. It is one of the strongest known acids. The 'Substance identity' section is calculated from substance identification information from all ECHA databases. Click on a date/time to view the file as it appeared at that time. farblose, stechend riechende, hygroskopische Flüssigkeit[1], löslich in Wasser[2] und polaren organischen Lösungsmitteln wie DMF, DMSO, Sulfolan, Acetonitril[4]. In electrophilic trifluoromethylation the active trifluoromethyl donor group carries a positive charge. Since ECHA aims to devote our maximum effort to this new system, we can no longer maintain REACH registration data on the current Dissemination Platform. 1.. IntroductionFriedel-Crafts reactions 2 are widely used in organic synthesis for carbon-carbon bond formation. In that case, the ATP (Adaptation to Technical Progress) number is displayed. If no EU harmonised classification and labelling exists and the substance was not registered under REACH, information derived from classification and labelling (C&L) notifications to ECHA under CLP Regulation is displayed under this section. In this reaction benzotrichloride was reacted with SbF3 to form PhCF2Cl and Harmonised classification and labelling is a legally binding classification and labelling for a substance, agreed at European Community level. InfoCards are updated when new information is available. Here you can find all of the regulations and regulatory lists in which this substance appears, according to the data available to ECHA. Triflic acid promotes other Friedel–Crafts-like reactions including the cracking of alkanes and alkylation of alkenes, which are very important to the petroleum industry. Allerdings kann in Estern, Ethern, Alkoholen oder Ketonen nicht immer davon ausgegangen werden, dass sich Trifluormethansulfonsäure inert gegenüber dem Lösungsmittel verhält. Chem. Für die Triflatgruppe wird in Fachpublikationen zumeist die Abkürzung „OTf“ verwendet; die Abkürzung „Tf“ steht für die Trifluormethansulfonylgruppe –SO2CF3, auch Triflylgruppe genannt. Find out more on how we use cookies. Trifluormethansulfonsäure wird aus Bis- (trifluormethyl)-disulfan in flüssiger Phase und in saurem Milieu mit einem sauerstoffhaltigen Oxidationsmittel hergestellt. In the McLoughlin-Thrower reaction (1962) iodobenzene reacts with trifluoroiodomethane (CF3I) and copper powder in dimethylformamide at 150 °C to trifluoromethylbenzene. Aromatic ketones have been prepared by the reaction of carboxylic acids with aromatic hydrocarbons catalyzed by a wide variety of catalysts (generally used in excess of molar amounts . The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). Trifluormethansulfonsäure raucht an der Luft, ist ätzend und muss dementsprechend vorsichtig gehandhabt werden. [13] Since then TMSCF3 has been widely used as a nucleophilic trifluoromethylating agent. Die Triflatgruppe findet in der organischen Chemie verbreitete Verwendung als Abgangsgruppe. Joachim K. Eberhard's 4 research works with 25 citations and 68 reads, including: Carbonsäure trifluormethansulfonsäure- und -methansulfonsäure-anhydride, Darstellung und Dissoziationstendenz Search Original file ‎(SVG file, nominally 723 × 227 pixels, file size: 80 KB). Hier finden Sie Informationen zu den Autoren des Artikels. Lizenz für Texte auf dieser Seite: CC-BY-SA 3.0 Unported. Diese Verbindung kann für ein breites Feld von Reaktionen verwendet werden, so Aldolreaktionen und Diels-Alder-Reaktionen (weitere Reaktionen siehe Namensreaktion oder Lewis-Säure). If generated, an InChI string will also be generated and made available for searching. Zudem sulfoniert die Trifluormethansulfonsäure keine Substrate, was bei Schwefelsäure durchaus passieren kann. In nucleophilic trifluoromethylation the active species is the CF3− anion. In the case of the β-leaving group, Fraser-Reid and co-workers have reported that the 3,4- or 2,3-cyclic spirodiacetal protecting group (dispoke) slowed down the hydrolysis of pent-4-enyl β-glycosides by keeping them out of the flat conformation and destabilizing the intermediate cation (Fig. Files are available under licenses specified on their description page. Chloride ligands can be converted to the corresponding triflates: This conversion is conducted in neat HOTf at 100 °C, followed by precipitation of the salt upon the addition of ether. However, substance notifications in the InfoCard are aggregated independently of the impurities and additives. [36] Variations include another CF3 donor potassium (trifluoromethyl)trimethoxyborate,[37] the use of aryl boronic acids[38][39] or the use of a trifluoromethyl sulfonium salt[40] or the use of a trifluoromethylcopper(I) phenanthroline complex. Trifluoromethanesulfonic acid reacts exothermically with metal carbonates, hydroxides, and oxides. Alle Methoden ergeben hohe Ausbeuten und können an die Vielzahl der Anhydride 1 aus Phosphor-, Phosphon- und Phosphinsäuren einerseits und Methansulfonsäure, Trifluormethansulfonsäure und Schwefelsäure-monoimidazolid . Triflatsalze werden in den letzten Jahren verstärkt und erfolgreich als Lewis-Säuren in vielen Reaktionen eingesetzt. Triflat ist nicht nukleophil. Die industrielle Herstellung geschieht über die elektrochemische Fluorierung von Methansulfonylchlorid. Eine Übersicht über verschiedene Reaktionen ist in der Literatur gegeben. Contrary to the popular belief, the CF3 anion, with [K(18-crown-6)]+ as a countercation, was produced and characterized by Prakash and coworkers. Als konjugierte Base einer Supersäure ist es ein sehr stabiles Anion. Hazard statements were adapted to improve readability and may not correspond textually to the hazard statements codes description in the European Union Specific Hazard Statements (EUH) or the. the electronic edition of the Official Journal of the European Union. Bei säurekatalysierten Dehydratisierungen bewirkt ein Zusatz von Trifluormethansulfonsäure eine sofortige Isomerisierung der gebildeten Alkene zugunsten des thermodynamisch stabileren Alkens. Das für das erfindungsgemäße Verfahren be- nötigte Ausgangsprodukt Bis-(trifluormethyl)-disul- . It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents. Dabei handelt es sich um eine radikalische Reaktion, beispielsweise mit SO3 oder SO2Cl2. [53] Here CF3− and DMF form an hemiaminolate adduct ([Me2NCH(O)CF3]K).[24][55][56][57]. [30][31], Many CF3-containing metal complexes have been prepared, and some are useful for trifluoromethylation. This website uses cookies to ensure you get the best experience on our websites. The ‘Substance identity’ section is calculated from substance identification information from all ECHA databases. Trifluormethansulfonsäure raucht an der Luft, ist ätzend und muss dementsprechend vorsichtig gehandhabt werden. [43] Reagents such as bromotrifluoromethane and haloform have been used for this purpose[44][45][46] but in response to the Montreal Protocol alternatives such as trifluoroiodomethane have been developed as replacement. It covers their hazardous properties, classification and labelling, and information on how to use them safely. Trifluoromethanesulfonic acid acts as a catalyst for esterification reactions and an acidic titrant in nonaqueous acid-base titration. [77][78] It reacts with acyl halides to prepare mixed triflate anhydrides, which are strong acylating agents used in Friedel-Crafts reactions. The source of the information is mentioned in the introductory sentence of the hazard statements. 193, p. 45. [14][15], An example is the trifluoromethylation of cyclohexanone in THF using tetrabutylammonium fluoride. B. Perchlorsäure oder Salpetersäure. In the field of electrophilic trifluoromethylation an early contribution involved reaction of a metal enolate with a trifluoromethyl chalcogen salt in presence of a chiral boron catalyst. Ayrl- 3 und Alkylsulfensäure-trifluormethansulfonsäure-anhydride 5 sind aus Sulfenylhalogeniden 1 bzw.4 und Silber-trifluormethansulfonate (2) in guten Ausbeuten zugänglich, wegen ihrer Zersetzlichkeit jedoch nicht in Substanz isolierbar.Aus den 1 H-NMR-Spektren der gemischten Anhydride 5a, b in Dichlormethan bzw. More information about Classification and Labelling is available in the Regulations section of ECHA website. H2O, melting point 34 °C. Die industrielle Herstellung geschieht über die elektrochemische Fluorierung von Methansulfonylchlorid. ECHA maintains the C&L Inventory, but does not review or verify the accuracy of the information. PhCF3. Arch. März 2023 um 20:41, Encyclopedia of Reagents for Organic Synthesis, https://de.wikipedia.org/w/index.php?title=Trifluormethansulfonsäure&oldid=231655699. If a substance is classified under multiple CLH entries, a link to the C&L Inventory is provided to allow users to view CLH information associated with the substance and no text is automatically generated for the InfoCard. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, Leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib and triflurazin. This website uses cookies to ensure you get the best experience on our websites. Another group of trifluoromethyl donors are hypervalent iodine(III)[65]–CF3 reagents for example 3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole. in case of consumer and professional uses). As such once the IUCLID format change begins on 19th May 2023 we will no longer update REACH registered substance factsheets. Because Ruppert's reagent requires a tetraalkylammonium fluoride, chiral ammonium fluorides have been employed in asymmetric catalysis. Donald J. Burton, Long Lu "Fluorinated Organometallic Compounds" Topics in Current Chemistry, 1997, Vol. This section is based on three sources for information (harmonised classification and labelling (CLH), REACH registrations and CLP notifications). Triflic acid is mainly used in research as a catalyst for esterification. [4] Sowohl die Säure als auch die konjugierte Base, das Triflatanion, sind resistent gegen die meisten Oxidations- und Reduktionsmittel, während viele andere starke Säuren oxidierend wirken, wie z. In the 1930s Kinetic Chemicals and IG Farben replaced SbF3 with HF. REACH registration dossiers have greater data requirements (such as supporting studies) than do notifications under CLP. [17][18] Potassium (trifluoromethyl)trimethoxyborate for this purpose has been synthesised from B(OMe)3, CF3SiMe3 and KF. [47][48] One particular combination is CF3I / triethylborane[49][50] [9] Nach günstigeren Synthesen wird weiterhin gesucht. Arbeit unter dem Abzug ist unbedingt erforderlich. Use of this information is subject to copyright laws and may require the permission of the owner of the information, as described in the ECHA Legal Notice. [34][35] The first copper catalysed coupling was reported in 2009 and based on an iodoarene, a trifluoromethylsilane, copper iodide and 1,10-phenanthroline. Triflic acid is one of the strongest acids. : The rates of many group transfers are well described by the Marcus equation.Alkyl transfers in the solvent sulfolane, the formal transfers of R+ from one nucleophile to another, fit almost within experimental error.In these fairly slow reactions the Marcus quadratic term is negligible.Neglect of this term leads to absence of Reactivity Selectivity principle correlations.It leads to a scale of nucleophilicities and one of methylating power.In contrast, many nonalkyl transfers have much lower intrinsic barriers, and neglect of the quadratic term is unjustifiable.For alkyl transfers there is no general correlation between rate and equilibrium constants.When closely related series, such as a Hammett variation in the leaving group or nucleophile are studied, there is generally a rate-equilibrium LFER.From the slope of this rate-equilibrium LFER, the charge, δ, on the transferring group is calculated.The variation in this charge, which is structurally plausible, gives a new perspective on the rates of SN2 reactions, including benzylic, and α-halocarbonyl systems. 423939 423939 Trifluormethansulfonsäure-phenylester Write a review 98% Synonym (s): Phenyltriflat Linear Formula: C6H5SO3CF3 CAS Number: 17763-67-6 Molecular Weight: 226.17 MDL-Nummer: MFCD00192399 PubChem Substanz-ID: 24866540 NACRES: NA.22 Pricing and availability is not currently available. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner. Examples of substrates that have been investigated are pyridine, aniline, triphenylphosphine and the lithium salt of phenylacetylene. B. AlCl3 nicht gegeben ist. Other relevant information includes the following: To see the full list of notified classifications and to get more information on impurities and additives relevant to classification please consult the C&L Inventory. Die Verbindung raucht an der Luft, wobei sich das stabile Monohydrat (eigentlich: Oxonium trifluormethylsulfonat) bildet, welches einen Schmelzpunkt von 36 °C besitzt und stark hygroskopisch ist. Please upgrade your Internet Explorer to a newer version. To begin with this system will take over the responsibility of making REACH registration data available, once it is ready. The type of uses and classifications may vary between different submissions to ECHA and for a full understanding it is recommended to consult the source data. pKs-Werte Liste alphabetisch sortiert ,nur Stoffe die S enthalten. These reagents are generated in situ by reaction of CF3I with copper powder in polar solvents. Close [4] Sowohl die Säure als auch die konjugierte Base, das Triflatanion, sind resistent gegen die meisten Oxidations- und Reduktionsmittel, während viele andere starke Säuren oxidierend wirken, wie z. Welcome to the ECHA website. Für weitergehende Informationen sei auf die Literatur verwiesen. Trimethylsilyl triflate (2.22 g, 1.93 ml, 10 mmol) was added to a stirred suspension of iodosylbenzene (2.2 g, 10 mmol) in dichloromethane (30 ml) at - 30 °C under nitrogen.The mixture was allowed to warm to − 5 °C and stirred until formation of a yellow solution.This was recooled to − 30 °C and trimethylsilyl cyanide (1.08 g, 1.45 ml, 11 mmol) was added via a syringe; the mixture was . Aus Trifluormethansulfonsäure können durch Zugabe von Säureanhydriden oder -chloriden gemischte Anhydride gewonnen werden. [7] Trifluormethylsulfonsäure findet in der organischen Chemie vielfältige Verwendung, die Triflatgruppe wird gern als Abgangsgruppe benutzt und ihre Salze kommen in Katalysatoren zum Einsatz. Löslichkeit It does not represent a new labelling, classification or hazard statement, neither reflect other factors that affect the susceptibility of the effects described, such as duration of exposure or substance concentration (e.g. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. It serves as a deglycosylation agent for glycoproteins. Substrates are thiols, alcohols, phosphines, (hetero) arenes,[70] unactivated olefins[71] and unsaturated carboxylic acids. The EC Number is the numerical identifier for substances in the EC Inventory. Este compuesto es un electrófilo . 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