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Key Documents

158534

Sigma-Aldrich

Trifluoromethanesulfonic acid

reagent grade, 98%

동의어(들):

TFMSA, Triflic acid

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About This Item

Linear Formula:
CF3SO3H
CAS Number:
Molecular Weight:
150.08
Beilstein:
1812100
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.21

Grade

reagent grade

Quality Level

vapor density

5.2 (vs air)

vapor pressure

8 mmHg ( 25 °C)

분석

98%

형태

liquid

refractive index

n20/D 1.327 (lit.)

bp

162 °C (lit.)

density

1.696 g/mL at 25 °C (lit.)

SMILES string

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

InChI

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

InChI key

ITMCEJHCFYSIIV-UHFFFAOYSA-N

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일반 설명

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.

애플리케이션

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

픽토그램

CorrosionExclamation mark

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

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

표적 기관

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point (°F)

>332.1 °F - Pensky-Martens closed cup

Flash Point (°C)

> 166.7 °C - Pensky-Martens closed cup

개인 보호 장비

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


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시험 성적서(COA)

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문서 라이브러리 방문

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)

문서

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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