Skip to Content
Merck
CN
All Photos(4)

Documents

Safety Information

T6508

Sigma-Aldrich

Trifluoroacetic acid

ReagentPlus®, 99%

Synonym(s):

TFA

Sign Into View Organizational & Contract Pricing
All Photos(4)

About This Item

Linear Formula:
CF3COOH
CAS Number:
76-05-1
Molecular Weight:
114.02
Beilstein:
742035
EC Number:
200-929-3
MDL number:
MFCD00004169
UNSPSC Code:
12352106
PubChem Substance ID:
329826846
NACRES:
NA.21

vapor density

3.9 (vs air)

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H332,H412

Hazard Classifications

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

WGK

WGK 2

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
View All Related Papers

Articles

Acid and Base Chart — Table of Acids & Bases

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

Fmoc resin cleavage and deprotection are crucial steps for peptide synthesis, yielding the desired peptide after resin detachment.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service