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158534

Sigma-Aldrich

Trifluoromethanesulfonic acid

reagent grade, 98%

Sinônimo(s):

TFMSA, Triflic acid

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About This Item

Fórmula linear:
CF3SO3H
Número CAS:
1493-13-6
Peso molecular:
150.08
Beilstein:
1812100
Número CE:
216-087-5
Número MDL:
MFCD00007514
Código UNSPSC:
12352100
ID de substância PubChem:
24849764
NACRES:
NA.21
Preço e disponibilidade não estão disponíveis no momento.

grau

reagent grade

Nível de qualidade

200

densidade de vapor

5.2 (vs air)

pressão de vapor

8 mmHg ( 25 °C)

Ensaio

98%

Formulário

liquid

índice de refração

n20/D 1.327 (lit.)

p.e.

162 °C (lit.)

densidade

1.696 g/mL at 25 °C (lit.)

grupo funcional

fluoro
triflate

cadeia de caracteres SMILES

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

InChI

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

chave InChI

ITMCEJHCFYSIIV-UHFFFAOYSA-N

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Descrição geral

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]

Aplicação

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]

acessório

Nº do produto
Descrição
Preços

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palavra indicadora

Danger

Frases de perigo

H290,H302,H314,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

8A - Combustible corrosive hazardous materials

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

>332.1 °F - Pensky-Martens closed cup

Ponto de fulgor (°C)

> 166.7 °C - Pensky-Martens closed cup

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
MKCV8787
MKCW0675
MKCV6010
WXBF4735V
MKCW9365

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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
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)
Tetrahedron, 49, 5351-5351 (1993)
M Arisawa et al.
Organic letters, 3(5), 763-764 (2001-03-22)
[reaction: see text]. Addition of dialkyl disulfides to terminal alkynes is catalyzed by a rhodium-phosphine complex and trifluoromethanesulfonic acid giving (Z)-bis(alkylthio)olefins stereoselectively.
Aromatic nitration with nitric acid and trifluoromethanesulfonic acid.
Coon CL, et al.
The Journal of Organic Chemistry, 38(25), 4243-4248 (1973)
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Artigos

Friedel–Crafts Acylation

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

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      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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    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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