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158534

Sigma-Aldrich

Trifluoromethanesulfonic acid

reagent grade, 98%

Sinonimo/i:

TFMSA, Triflic acid

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10 G
CHF 35.60
50 G
CHF 103.00
100 G
CHF 163.00

CHF 35.60

Spedizione prevista il21 maggio 2025

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Cambia visualizzazione
10 G
CHF 35.60
50 G
CHF 103.00
100 G
CHF 163.00

About This Item

Formula condensata:
CF3SO3H
Numero CAS:
1493-13-6
Peso molecolare:
150.08
Beilstein:
1812100
Numero CE:
216-087-5
Numero MDL:
MFCD00007514
Codice UNSPSC:
12352100
ID PubChem:
24849764
NACRES:
NA.21

CHF 35.60

Spedizione prevista il21 maggio 2025

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Grado

reagent grade

Livello qualitativo

200

Densità del vapore

5.2 (vs air)

Tensione di vapore

8 mmHg ( 25 °C)

Saggio

98%

Stato

liquid

Indice di rifrazione

n20/D 1.327 (lit.)

P. ebollizione

162 °C (lit.)

Densità

1.696 g/mL at 25 °C (lit.)

Gruppo funzionale

fluoro
triflate

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.[1] 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.[1] On mixing trifluoromethanesulfonic acid with HNO3, it forms nitronium trifluoromethane sulfonate, which is an excellent nitrating reagent.[2]

Applicazioni

Deglycosylation agent
Trifluoromethanesulfonic acid is a versatile reagent[3], employed as catalyst for the following studies:
  • Friedel-Crafts acylation of aromatic compounds with methyl benzoate.[4]
  • Addition reaction of dialkyl disulfides to terminal alkynes.[5]
  • Synthesis of a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side-chain groups (Am-CyTS).[6]
  • Preparation of starting reagents for the synthesis of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives.[7]
  • Synthesis of aryl triflates,[8] the lactonization of alkenoic acids,[9] and the formation of E-alkenes.[10]
Trifluoromethanesulfonic acid may be used as an initiator for the cationic polymerization of styrene[11], hexamethylcyclotrisiloxane[12] and L,L-dilactide.[13]

Accessorio

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

CorrosionExclamation mark
GHS05,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H290,H302,H314,H335

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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Certificati d'analisi (COA)

Lot/Batch Number
MKCV8787
MKCW0675
MKCV6010
WXBF4735V
MKCW9365

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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
Tetrahedron, 49, 7119-7119 (1993)
Synthesis, 735-735 (1993)
Meilin Li et al.
Archiv der Pharmazie, 348(5), 353-365 (2015-04-01)
A new series of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives were synthesized from starting compounds 3a-i, which were prepared from acrylic acid ethyl ester and the appropriate amines using trifluoromethanesulfonic acid as a catalyst. A total of 9 novel derivatives were synthesized
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Articoli

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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