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Key Documents

158534

Sigma-Aldrich

Trifluoromethanesulfonic acid

reagent grade, 98%

Sinonimo/i:

TFMSA, Triflic acid

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About This Item

Formula condensata:
CF3SO3H
Numero CAS:
Peso molecolare:
150.08
Beilstein:
1812100
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.21

Grado

reagent grade

Livello qualitativo

Densità del vapore

5.2 (vs air)

Tensione di vapore

8 mmHg ( 25 °C)

Saggio

98%

Forma fisica

liquid

Indice di rifrazione

n20/D 1.327 (lit.)

P. eboll.

162 °C (lit.)

Densità

1.696 g/mL at 25 °C (lit.)

Stringa SMILE

OS(=O)(=O)C(F)(F)F

InChI

1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)
ITMCEJHCFYSIIV-UHFFFAOYSA-N

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Descrizione generale

Trifluoromethanesulfonic acid is the strongest monoprotic organic acid. It has been synthesized by the oxidation of bis(trifluoromethylthio)mercury with aqueous hydrogen peroxide. It undergoes complete dissociation in basic solvents such as dimethyl sulfoxide, dimethylacetamide and dimethylformamide. Its dissociation in non-aqueous solvents has been studied by conductometry. On mixing trifluoromethanesulfonic acid with HNO3, it forms nitronium trifluoromethane sulfonate, which is an excellent nitrating reagent.

Applicazioni

Trifluoromethanesulfonic acid is a versatile reagent, employed as catalyst for the following studies:
  • Friedel-Crafts acylation of aromatic compounds with methyl benzoate.
  • Addition reaction of dialkyl disulfides to terminal alkynes.
  • Synthesis of a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side-chain groups (Am-CyTS).
  • Preparation of starting reagents for the synthesis of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives.
  • Synthesis of aryl triflates, the lactonization of alkenoic acids, and the formation of E-alkenes.
Trifluoromethanesulfonic acid may be used as an initiator for the cationic polymerization of styrene, hexamethylcyclotrisiloxane and L,L-dilactide.
Deglycosylation agent

Accessorio

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

CorrosionExclamation mark

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 4 Oral - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

>332.1 °F - Pensky-Martens closed cup

Punto d’infiammabilità (°C)

> 166.7 °C - Pensky-Martens closed cup

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Tetrahedron, 49, 5351-5351 (1993)
Polylactones, 8. Mechanism of the cationic polymerization of L, L-dilactide.
Kricheldorf HR and Dunsing R.
Macromolecular Chemistry and Physics, 187(7), 1611-1625 (1986)
Cationic polymerization of hexamethylcyclotrisiloxane by trifluoromethanesulfonic acid and its derivatives, 2. Reaction involving activated trifluoromethylsulfonates.
Toskas G, et al.
Macromolecular Chemistry and Physics, 196(9), 2715-2735 (1995)
Shota Kinoshita et al.
Journal of the American Chemical Society, 137(15), 5061-5065 (2015-04-01)
In this study, a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side-chain groups (Am-CyTS) was selectively prepared by the hydrolytic condensation of 3-aminopropyldiethoxymethylsilane using aqueous superacid trifluoromethanesulfonic acid. The (1)H NMR spectrum of Am-CyTS in D2O exhibited a single
Determination of the rate constants of the elementary steps in the cationic polymerization of styrene by trifluoromethanesulfonic acid.
Kunitake T and Takarabe K.
Macromolecules, 12(6), 1061-1067 (1979)

Articoli

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

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