Trifluormethansulfonsaeureanhydrid
Tf2O · TRIFLIC ANHYDRIDE · Trifluoromethylsulfonic anhydride · TFO2 · trifluoromethylsulfonyl trifluoromethanesulfonate · TRIFLUOROMETHANESULFONIC ACID ANHYDRIDE · TRIFLUOROMETHANESULPHONIC ANHYDRIDE · (trifluoroMethane)sulfonyl trifluoroMethanesulfonate
Identifikatoren & physikalische Daten
| CAS No. | 358-23-6 |
|---|---|
| Summenformel | C2F6O5S2 |
| Durchschnittliche Molmasse | 282,14 g/mol |
| Monoisotopische Masse | 281,90913442 g/mol |
| SMILES | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F |
| InChIKey | WJKHJLXJJJATHN-UHFFFAOYSA-N |
| PubChem CID | 67749 |
| ChEBI | CHEBI:48509 |
| EC No. | 206-616-8 |
| DTXSID | DTXSID501014629 |
| Lokaler Name | Trifluormethansulfonsaeureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 94,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 11 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 370 |
| Stoffklassen | Other Classes -> Acid Anhydrides, Other |
| PFAS | PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compoundsPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008 |
| SpringerMaterials Properties | Schoenflies notation |
| Dichte | 1.677 @25 °C1.677 g/mL at 25 °C (lit.) |
| Dampfdruck | 8.0 [mmHg]8 [mm Hg] @20 °C8 mm Hg ( 20 °C) |
| Physical Description | Colorless hygroscopic liquid[Merck Index] Clear colorless liquid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | -80°C |
| Siedepunkt | 81-83 °C (lit.) |
| Dampfdichte | 5.2 (vs air) |
| Brechungsindex | n20/D 1.321(lit.) |
| Flammpunkt | 81-83°C |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Miscible with dichloromethane. Immiscible with hydrocarbons.reacts violently with water |
| Aggregatzustand | Liquid |
| Wichte | 1.677 |
| Farbe | Clear colorless to light brown |
| BRN | 1813600 |
| Stabilität | Hygroscopic, Moisture Sensitive |
| InChI | 1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8 |
| InChIKey | WJKHJLXJJJATHN-UHFFFAOYSA-N |
| SMILES | FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F |
| LogP (Verteilungskoeffizient) | 0.3 at 25℃ |
| CAS Datenbank | 358-23-6(CAS DataBase Reference) |
| NIST chemische Informationen | Trifluoromethanesulfonic anhydride(358-23-6) |
| EPA chemische Informationen | Methanesulfonic acid, trifluoro-, anhydride (358-23-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH272 (51.1%): May intensify fireoxidizer [Danger Oxidizing liquidsOxidizing solids]P210, P220, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 227 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Methanesulfonic acid, trifluoro-, anhydrideStatus: Active Update: 03-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/22478Trifluoromethanesulphonic anhydride: HSNO Approval: HSR004747 Approved with controls |
| Gefahrenübersicht | Reacts violently with waterCorrosive[Merck Index] Reacts violently with waterCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion[Sigma-Aldrich MSDS] See Trifluoromethanesulfonic acid. |
| Hazard Classes and Categories | Ox. Liq. 2 (51.1%) |
| CSL Reaction Information | CSL00005TETRAHYDROFURAN + Triflic anhydrideCan polymerize, large exotherm. Avoid combination on larger scale.User-Reported6/29/1810/2/17 |
| Protective Action Criteria (PAC) | 3.0 [mg/m3]33 [mg/m3]200 [mg/m3] |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3265 8/PG 2 |
| Zollcode | 29049020 |
| R-Sätze (R) | 14-21/22-34-35-22-40 |
| Toxizität | LD50 orally in Rabbit: 1012 mg/kg |
| Gefahrensymbole | C |
| hazard_note | Corrosive |
| Sicherheitshinweise (S) | 26-36/37/39-43-45-8 |
| Gefahrenklasse | 8Acute Tox. 4 OralEye Dam. 1Ox. Liq. 2Skin Corr. 1BSTOT SE 3 |
| Verpackungsgruppe | I |
| Lagerklasse | 5.1B - Oxidizing hazardous materials |
Anwendungen & Verwendung
Beschreibung
Trifluoromethanesulfonic anhydride, also known as triflic anhydride, has proven to be an extraordinary reagent for a broad range of transformations. As a commercially and readily available reagent, It has been widely used in synthetic chemistry due to its high electrophilicity. Given its high affinity towards O-nucleophiles, reaction with alcohols, carbonyls, sulfur phosphorus- and iodine oxides towards the formation of the corresponding triflates is strongly favored. As one of the premier leaving groups in organic chemistry, the generated triflates then open the door to various downstream transformations, including (but not limited to) substitution reactions, cross-coupling processes, redox reactions, and rearrangements[1-2].
Verwenden
Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.