8.08260

Trifluoroacetic acid

for synthesis

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

Properties

• 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

Description

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

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H314,H332,H412
• pcodes: P261 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1A
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 2
• flash_point_f: >212.0 °F - Pensky-Martens closed cup
• flash_point_c: > 100 °C - Pensky-Martens closed cup