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8.08260

Sigma-Aldrich

Trifluoroacetic acid

for synthesis

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Synonym(s):
TFA
Linear Formula:
CF3COOH
CAS Number:
76-05-1
Molecular Weight:
114.02
Beilstein:
742035
MDL number:
MFCD00004169
UNSPSC Code:
12352106
EC Index Number:
200-929-3
NACRES:
NA.22

vapor density

3.9 (vs air)

Quality Level

200

vapor pressure

97.5 mmHg ( 20 °C)

Assay

≥99% (acidimetric)

form

liquid

refractive index

n20/D 1.3 (lit.)

pH

1 (10 g/L in H2O)

bp

72.4 °C (lit.)

mp

−15.4 °C (lit.)

solubility

soluble 10 g/mL

density

1.489 g/mL at 20 °C (lit.)

storage temp.

2-30°C

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 is widely used in organic synthesis as a solvent, catalyst and reagent. It is a strong acid and low boiling point reagent. It can be used as a catalyst for a variety of reactions such as rearrangements, functional group deprotections, oxidations, reductions, condensations, hydroarylations and trifluoromethylations.

Application

Trifluoroacetic acid can be used as a catalyst

  • In the direct conversion of cyclohexanone to caprolactam using acetonitrile as the additive.
  • In the synthesis of 1,2,4,5-tetrasubstituted imidazoles by four-component condensation of benzil, aldehydes, amines, and ammonium acetate.
Trifluoroacetic acid can also be used
  • In the synthesis of d-α-Tterpineo from d-limonene by Markovnikov addition followed by hydrolysis.

Features and Benefits

Trifluoroacetic acid can be used as a catalyst due to its
  • High acidity
  • Easy elimination
  • Good solubility in organic solvent and in water.

Analysis Note

Assay (acidimetric): ≥ 99.0 %
Density (d 20 °C/ 4 °C): 1.487 - 1.490
Identity (IR): passes test

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)

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Trifluoroacetic acid as an efficient catalyst for one-pot, four-component synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles under microwave-assisted, solvent-free conditions
Mohammadizadeh MR, et al.
Synthetic Communications, 39(18), 3232-3242 (2009)
A Practical Synthesis of?d-?-Terpineol via Markovnikov Addition of?d-Limonene Using Trifluoroacetic Acid
Yuasa Y, et al.
Organic Process Research & Development, 10(6), 1231-1232 (2006)
Trifluoroacetic acid: Uses and recent applications in organic synthesis
Lopez SE, et al.
Journal of Fluorine Chemistry, 156, 73-100 (2013)

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