Trifluoroacetic Acid

Base Information

• Chemical Name: Trifluoroacetic Acid
• CAS No.: 76-05-1
• Molecular Formula: C2HF3O2
• Molecular Weight: 114.024
• Hs Code.: 2915.90
• European Community (EC) Number: 200-929-3
• ICSC Number: 1673
• NSC Number: 77366
• UN Number: 2699
• UNII: E5R8Z4G708
• DSSTox Substance ID: DTXSID9041578
• Nikkaji Number: J2.401E
• Wikipedia: Trifluoroacetic_acid
• Wikidata: Q412033
• NCI Thesaurus Code: C84228
• ChEMBL ID: CHEMBL506259
• Mol file: 76-05-1.mol

Synonyms:Acid, Trifluoroacetic;Cesium Trifluoroacetate;Trifluoroacetate;Trifluoroacetate, Cesium;Trifluoroacetic Acid

Chemical Property of Trifluoroacetic Acid

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 97.5 mm Hg ( 20 °C)
• Melting Point: -15 °C
• Refractive Index: n20/D 1.3(lit.)
• Boiling Point: 72.245 °C at 760 mmHg
• PKA: -0.3(at 25℃)
• Flash Point: -2.506 °C
• PSA: 37.30000
• Density: 1.571 g/cm³
• LogP: 0.63330
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Miscible with ether, acetone, ethanol, benzene, hexane, and CCl&
• Water Solubility.: miscible
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 113.99286376
• Heavy Atom Count: 7
• Complexity: 83.4
• Transport DOT Label: Corrosive

Purity/Quality:

95+% ^*data from raw suppliers

Trifluoroacetic acid 99+.9% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, T, Xi
• Hazard Codes: C,T,Xi
• Statements: 20-35-52/53-34
• Safety Statements: 9-26-27-28-45-61-28A-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: PFAS,Other Classes -> Organic Acids
• Canonical SMILES: C(=O)(C(F)(F)F)O
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of fumes may cause lung oedema.
• description: Trifluoroacetic acid (TFA, molecular formula: CF3COOH) is a kind of colorless, volatile and fuming liquid with a similar odor as acetic acid. It is hygroscopic and has irritating odor. It has strong acidic property due to being affected by the electron-attracting trifluoromethyl group with its acidicity being 100000 higher than acetic acid. It has a melting point being-15.2 ℃, boiling point being 72.4 ℃, and the density being 1.5351g/cm3 (1℃). It is miscible with water, fluorinated hydrocarbons, methanol, ethanol, ethyl ether, acetone, benzene, carbon tetrachloride, and hexane; it is partially soluble in carbon disulfide and alkane containing more than six carbons. It is an excellent solvent of protein and polyester. Trifluoroacetic acid is also a good solvent for the organic reaction which allows obtaining certain results which are difficult in the cases of application of common solvents. For example, when quinolone is being catalyzed for hydrogenation in a common solvent, the pyridine ring is preferentially hydrogenated; in contrast, the benzene ring will be preferentially hydrogenated in the presence of trifluoroacetic acid as the solvent. Trifluoroacetic acid is decomposed into carbon dioxide and fluorine in the presence of aniline. It can be reduced by sodium borohydride or lithium aluminum hydride into trifluoroacetic acetaldehyde and trifluoro-ethanol. It is stable at temperature higher than 205 ℃ stable. But its ester and amides derivatives are easily subject to hydrolysis which allows them to prepare carbohydrate, amino acids, and peptide derivative in the form of acid or anhydride. It is easily to be dehydrated under action of phosphorus pentoxide and be converted to trifluoroacetic anhydride. Trifluoroacetic acid is a kind of important intermediates of fat fluorine. Owing to the special structure of trifluoromethyl, it has a different property from other alcohols and can participate in a variety of organic reactions, especially being used in the field of the synthesis of fluorine-containing pharmaceutical, pesticides and dyes. Its domestic and foreign demand is increasing and has become one of the important intermediates for fluorine-containing fine chemicals.
• uses: Trifluoroacetic acid is mainly for the production of new pesticide, medicine and dyes, and also has great potential of application and development in the fields of materials and solvents. Trifluoroacetic acid is mainly used for the synthesis of various kinds of trifluoromethyl group or heterocyclic containing herbicides. It is currently available for synthesizing various kinds of novel herbicide containing pyridyl and qunoilyl; acting as a strong proton acid, it is widely applied as the catalyst for alkylation, acylation, and olefin polymerization of aromatic compound; as a solvent, trifluoroacetic acid is a kind of excellent solvent for fluorination, nitration and halogenations. In particular, the excellent protective effect of its trifluoroacetyl derivatives on hydroxy and amino group has very important application in the synthesis of amino acid and poly-peptide synthesis, for example, the compound can be used as the protection agent of tert-butoxycarbonyl (t-boc) which is used for removing amino acids during the synthesis of poly-peptide. Trifluoroacetic acid, as the raw material and modifier for the preparation of the ion membrane, can largely improve the current efficiency of soda industry and significantly extend the working life of the membrane; trifluoroacetic acid can also be used for synthesizing trifluoro-ethanol, trifluoroacetic acetaldehyde and trifluoroacetic anhydride. At room temperature, the mercury trifluoroacetic acid can have mercury-fluorophenyl be able to have mercuration reaction (electrophilic substitution), and can also convert hydrazone to diazo compound. The lead salt of this acid can convert arene to phenol. In the experiment of reverse phase chromatography for isolation of peptides and proteins, using trifluoroacetic acid (TFA) as the ion-pairing reagents is a common approach. Trifluoroacetic acid in the mobile phase can improve the peak shape and overcome the problem of the peak broadening and trailing issue through interaction with hydrophobic bonded phase and residual polar surface in a variety of models. Trifluoroacetic acid has an advantage over other ion modifier due to that it is volatile and can be easily removed from the sample preparation. On the other hand, the maximum UV absorption peak of trifluoroacetic acid is less than 200 nm, and thus having very small interference on the detection of polypeptides at low wavelengths.
• Uses: Trifluoroacetic acid is an important building block in the synthesis of pharmaceuticals, agrochemicals and performance products. It is a precursor to many fluorinated compounds, and widely used in peptide synthesis and other organic transformations involving deprotection of t-BOC group. The combination of properties like solubility in most of the solvents, volatility, catalytic property, and strong acidity with non-oxidizing nature makes it a widely used reagent in organic synthesis. Trifluoroacetic acid can use as an ion pairing agent in liquid chromatography, as a solvent in NMR spectroscopy and as a calibrant in mass spectrometry. It is used as a catalyst in esterification reaction and condensation reaction and a protective agent for hydroxyl and amino.

Technology Process of Trifluoroacetic Acid

There total 315 articles about Trifluoroacetic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C8F14O6 (1204186-49-1) → difluoro((2,2,4,5-tetrafluoro-5-(trifluoromethoxy)-1.3-dioxolan-4-yl)oxy)acetic acid (1190931-41-9) + trifluoroacetic acid (76-05-1)

Guidance literature:

With water; at 0 ℃;

Reference yield: 85.0%

1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) → 1,1,1-trifluoro-2-propanone (421-50-1) + 1,1,1,5,5,5-hexafluoro-2-aminopentan-4-one + trifluoroacetic acid (76-05-1)

Guidance literature:

With ammonia; at 80 ℃; for 3h;

DOI:10.1016/S0022-1139(00)80908-2

Reference yield: 78.0%

octafluoroacetophenone (652-22-2) → Pentafluorobenzene (363-72-4) + trifluoroacetic acid (76-05-1)

Guidance literature:

With water; potassium carbonate; at 80 ℃; for 2h;

DOI:10.1016/j.jfluchem.2021.109851

upstream raw materials:

tetrachloromethane

tert-butyl trifluoroperoxyacetate

trifluoracetyl chloride

silver(I) cyanide

Downstream raw materials:

3-benzoyl-2,6-dimethyl-4-pyrone

2,6-dibromopyridin N-oxide

2-acetoxymethyl-5-benzoyloxy-pyran-4-one

trifluoracetyl chloride

Refernces

• 1、 George,Saison,Ponche,Mirabel. "Kinetics of mass transfer of carbonyl fluoride, trifluoroacetyl fluoride, and trifluoroacetyl chloride at the air/water interface". . p. 10857 - 10862. Retrieved 1994.
• 2、 Banks,Burling. "-". . p. 6077,6082. Retrieved 1965.
• 3、 Allen. "-". . p. 923. Retrieved 1961.
• 4、 Schuster, Ingeborg I.,Freyer, Alan J.,Rheingold, Arnold L.. "N- vs O-protonation and the transannular substituent interaction in 8-(dimethylamino)-1-acetonaphthone". . p. 5752 - 5759. Retrieved 2000.
• 5、 Zonov, Yaroslav V.,Wang, Siqi,Karpov, Victor M.,Mezhenkova, Tatyana V.. "The aliphatic ring-opening and SNAr substitution in the reactions of perfluorobenzocycloalkenones with K2CO3 in water and methanol". . . Retrieved 2021/07/28.
• 6、 Kirihara, Masayuki,Suzuki, Katsuya,Nakakura, Kana,Saito, Katsuya,Nakamura, Riho,Tujimoto, Kazuki,Sakamoto, Yugo,Kikkawa, You,Shimazu, Hideo,Kimura, Yoshikazu. "Oxidation of fluoroalkyl alcohols using sodium hypochlorite pentahydrate [1]". . . Retrieved 2021/02/05.