Merck
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T6508

Sigma-Aldrich

Trifluoroacetic acid

ReagentPlus®, 99%

Synonym(s):
TFA
Linear Formula:
CF3COOH
CAS Number:
Molecular Weight:
114.02
Beilstein:
742035
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

vapor density

3.9 (vs air)

Quality Level

vapor pressure

97.5 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99%

form

liquid

impurities

≤0.05% water

refractive index

n20/D 1.3 (lit.)

pH

1 (10 g/L)

bp

72.4 °C (lit.)

mp

−15.4 °C (lit.)

solubility

ethanol: soluble 0.33 mL/mL

density

1.489 g/mL at 20 °C (lit.)

SMILES string

OC(C(F)(F)F)=O

InChI

1S/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7)

InChI key

DTQVDTLACAAQTR-UHFFFAOYSA-N

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General description

Trifluoroacetic acid (TFA) is an organofluorine compound used as a reagent in organic synthesis for various acid-catalyzed reactions such as ring-opening of epoxides, biomimetic cyclization, Cope rearrangements, and natural product synthesis. TFA′s physicochemical characteristics provide advantages over other acids because of its high volatility, solubility in organic solvents, and acidic strength. When TFA is used as a reagent the product isolation is simple by evaporation due to its very high volatility. Less volatile acids such as sulfuric acid or p-toluenesulfonic acid may require neutralization or an extractive workup.[1]

Application

Trifluoroacetic acid can be used as a reagent:      
  • For the cleavage of nitrogen and oxygen protecting groups such as N-Boc, N-benzyloxymethyl, benzyl ether, p-methoxybenzyl ether, t-butyl ether, t-butyloxymethyl ether, triphenylmethyl ether, and dimethyl acetals.[1][2][3]      
  • In the Baeyer–Villiger oxidation reactions in combination with sodium percarbonate.[1],·      
  • For the C-H trifluoromethylation of arenes.[4]

TFA can also be used as:      
  • A solvent in atom transfer cyclization reactions and polymer processes.[2]      
  • A catalyst in the synthesis of ε-caprolactam via Beckmann rearrangement of cyclohexanone oxime in aprotic solvents.[5]

Packaging

1, 10, 5×10, 10×10 amp in ampule
5, 25, 100, 4×100, 500 mL in glass bottle
1, 2 L in glass bottle
1mL in each ampule.

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1A

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

212.0 °F - Pensky-Martens closed cup

Flash Point(C)

> 100 °C - Pensky-Martens closed cup

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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