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T6508

Sigma-Aldrich

Trifluoroacetic acid

ReagentPlus®, 99%

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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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1 of 4

This Item
9170729953780457
vibrant-m

T6508

Trifluoroacetic acid

vibrant-m

91707

Trifluoroacetic acid

vibrant-m

299537

Trifluoroacetic acid

vibrant-m

80457

Trifluoroacetic acid

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

pH

1 (10 g/L)

pH

1 (20 °C, 1 g/L)

pH

1 (20 °C, 10 g/L)

pH

-

vapor density

3.9 (vs air)

vapor density

3.9 (vs air)

vapor density

3.9 (vs air)

vapor density

3.9 (vs air)

vapor pressure

97.5 mmHg ( 20 °C)

vapor pressure

97.5 mmHg ( 20 °C)

vapor pressure

97.5 mmHg ( 20 °C)

vapor pressure

97.5 mmHg ( 20 °C)

refractive index

n20/D 1.3 (lit.)

refractive index

n20/D 1.3 (lit.)

refractive index

n20/D 1.3 (lit.)

refractive index

n20/D 1.3 (lit.)

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.

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.      
  • In the Baeyer–Villiger oxidation reactions in combination with sodium percarbonate.,·      
  • For the C-H trifluoromethylation of arenes.

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

Packaging

1mL in each ampule.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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


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Organocatalyzed Beckmann rearrangement of cyclohexanone oxime by trifluoroacetic acid in aprotic solvent
Ronchin L, et al.
Catalysis Communications, 10(2), 251-256 (2008)
Oxidative C-C bond cleavage of N-alkoxycarbonylated cyclic amines by sodium nitrite in trifluoroacetic acid
Onomura O, et al.
Tetrahedron Letters, 49(47), 6728-6731 (2008)
Electronic effects in the acid-promoted deprotection of N-2, 4-dimethoxybenzyl maleimides
Watson DJ, et al.
Tetrahedron Letters, 42(10), 1827-1830 (2001)
Trifluoroacetic acid: Uses and recent applications in organic synthesis.
Lopez SE and Salazar J.
Journal of Fluorine Chemistry, 156, 73-100 (2013)
Guangfa Shi et al.
Organic letters, 17(1), 38-41 (2014-12-18)
Direct trifluoromethylation of arenes using TFA as the trifluoromethylating reagent was achieved with Ag as the catalyst. This reaction not only provides a new protocol for aryl C-H trifluoromethylation, but the generation of CF3· from TFA may prove useful in

Articles

Acid and base chart lists the strength of acids and bases (strongest to weakest) in order. Simple to use laboratory reference chart for scientists, researchers and lab technicians.

Protocols

Fmoc resin cleavage and deprotection follows the difficult task of detaching the peptide from the resin support and removing all the side-chain protecting groups of the amino acid residues to yield the desired peptide.

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