TRIFLUOROACETIC ACID
Trifluoroacetic acid
CAS: 76-05-1
Molecular Formula: C2HF3O2
TRIFLUOROACETIC ACID - Names and Identifiers
| Name | Trifluoroacetic acid |
| Synonyms | TFA WASH BUFFER trifluoraceticacid Trifluoressigs~ure RARECHEM AL BO 0421 Perfluoroaceticacid Trifluoracetic acid PERFLUOROACETIC ACID TRIFLUOROACETLC ACID TRIFLUOROACETIC ACID Trifluoroacetic acid trifluoro-aceticacid Trifluoroethanoicacid kyselinatrifluoroctova Aceticacid, trifluoro- trifluoroacetetic acid Kyselina trifluoroctova Chlorinated Paraffin-52 R3, TRIFLUOROACETIC ACID R4A, TRIFLUOROACETIC ACID Trifluoroaceticacidmincolorlessliq |
| CAS | 76-05-1 |
| EINECS | 200-929-3 |
| InChI | InChI=1/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7) |
| InChIKey | DTQVDTLACAAQTR-UHFFFAOYSA-N |
TRIFLUOROACETIC ACID - Physico-chemical Properties
| Molecular Formula | C2HF3O2 |
| Molar Mass | 114.02 |
| Density | 1.489 g/mL at 20 °C (lit.) |
| Melting Point | -15.4 °C (lit.) |
| Boling Point | 72.4 °C (lit.) |
| Flash Point | None |
| Water Solubility | miscible |
| Solubility | Miscible with ether, acetone, ethanol, benzene, hexane, and CCl4 |
| Vapor Presure | 97.5 mm Hg ( 20 °C) |
| Vapor Density | 3.9 (vs air) |
| Appearance | Liquid |
| Specific Gravity | 1.480 |
| Color | Colorless |
| Odor | Sharp, pungent odor |
| Maximum wavelength(λmax) | ['λ: 260 nm Amax: 0.9', , 'λ: 270 nm Amax: 0.10', , 'λ: 280 nm Amax: 0.05', , 'λ: 290 |
| Merck | 14,9681 |
| BRN | 742035 |
| pKa | -0.3(at 25℃) |
| PH | 1 (10g/l, H2O) |
| Storage Condition | Store at +15°C to +25°C. |
| Stability | Stable. Incompatible with combustible material, strong bases, water, strong oxidizing agents. Non-combustible. Hygroscopic. May react violently with bases. |
| Sensitive | Hygroscopic |
| Refractive Index | n20/D 1.3(lit.) |
| Physical and Chemical Properties | Character colorless volatile fuming liquid. Odor similar to acetic acid. Hygroscopic and irritating odor. melting point -15.6 ℃ boiling point 71.1 ℃ relative density 1.489 refractive index 1.2850 BR> solubility and water, fluoroalkanes, methanol, benzene, ether, carbon tetrachloride and hexane are miscible. Can partially dissolve more than six carbon alkanes and carbon disulfide. |
| Use | Used as pharmaceuticals, pesticide intermediates, biochemical reagents, Organic Synthesis Reagents |
TRIFLUOROACETIC ACID - Risk and Safety
| Risk Codes | R20 - Harmful by inhalation R35 - Causes severe burns R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R34 - Causes burns |
| Safety Description | S9 - Keep container in a well-ventilated place. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S27 - Take off immediately all contaminated clothing. S28 - After contact with skin, wash immediately with plenty of soap-suds. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S28A - S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 2699 8/PG 1 |
| WGK Germany | 2 |
| RTECS | AJ9625000 |
| FLUKA BRAND F CODES | 3 |
| TSCA | T |
| HS Code | 29159080 |
| Hazard Note | Toxic/Corrosive |
| Hazard Class | 8 |
| Packing Group | I |
| Toxicity | LD50 i.v. in mice: 1200 mg/kg (Airaksinen, Tammisto) |
TRIFLUOROACETIC ACID - Upstream Downstream Industry
| Raw Materials | benzotrifluoride |
| Downstream Products | Ethyl trifluoroacetate ethyl 4,4,4-trifluoroacetoacetate lisinopril |
TRIFLUOROACETIC ACID - Reference
| Reference Show more | 1. [IF=9.381] Ya Zhao et al."Polysaccharide from vinegar baked radix bupleuri as efficient solubilizer for water-insoluble drugs of Chinese medicine."Carbohyd Polym. 2020 Feb;229:115473 |
TRIFLUOROACETIC ACID - Comparision with trichloroacetic acid
Trifluoroacetic acid and trichloroacetic acid are both carboxylic acids, but they differ in acidity.
Trifluoroacetic acid (CF3COOH) is a stronger acid with a pKa value of about 0.23-0.27. Due to the presence of three fluorine atoms, trifluoroacetic acid has lower electron density, which increases its polarity and overall acidity.
Trichloroacetic acid (CCl3COOH) has a pKa value of approximately 0.92, making it weaker in comparison to trifluoroacetic acid. With three chlorine atoms, trichloroacetic acid has higher electron density, resulting in reduced polarity and weaker acidity.
In summary, trifluoroacetic acid is stronger in acidity compared to trichloroacetic acid.
Last Update：2024-04-09 19:55:45
TRIFLUOROACETIC ACID - comparision with formic acid
Trifluoroacetic acid has a higher acidity than formic acid. The acidity of trifluoroacetic acid is attributed to the electronegativity of the fluorine atoms present in the molecule, which can release negative charges more easily, making trifluoroacetic acid more acidic than formic acid.
Last Update：2024-04-09 19:55:45
TRIFLUOROACETIC ACID - mobile phase
The main functions of trifluoroacetic acid (TFA) in the mobile phase include:
Adjusting pH: Trifluoroacetic acid is a strong acid that can regulate the pH value of the eluent, which is crucial for peptide separation as the stability of peptides is usually related to their pI.
Enhanced separation efficiency: As an ion pair reagent, trifluoroacetic acid can interact with peptides, enhance separation efficiency, improve peak shape, and overcome peak broadening and tailing issues.
Improving mass spectrometry analysis: In the experiment of separating peptides and proteins by reverse phase chromatography, the use of trifluoroacetic acid as an ion pair reagent is a common method. It can remain on the surface of the reverse phase stationary phase and interact with peptides and column beds, which helps optimize separation conditions.
Adjusting selectivity: By changing the concentration of trifluoroacetic acid, the selectivity of peptides on reverse phase chromatography can be finely adjusted, which is very beneficial for optimizing separation conditions and increasing the information content of complex chromatographic analysis.
Inhibition of ion production: The mobile phase containing trifluoroacetic acid has an inhibitory effect on ion production, which may to some extent reduce the sensitivity and analytical quality of liquid chromatography-mass spectrometry technology. The post column addition technique can partially overcome this inhibitory effect, but it can complicate the chromatographic system. Reducing the concentration of trifluoroacetic acid can eliminate this inhibitory effect, but it can also lead to a decrease in the quality of chromatographic analysis.
The concentration of trifluoroacetic acid is usually not more than 0.5%, as it can make the pH of water reach below 2, with high ion strength and certain ion pairing effects.
Last Update：2024-04-09 19:55:45
TRIFLUOROACETIC ACID - Nature
Open Data Verified Data
strong irritating colorless liquid. Soluble in water, ethanol, ether. It is a good solvent for many organic compounds, such as carbon disulfide in combination, can dissolve protein. Non-combustible. Toxic gases are released by thermal decomposition or contact with acids. Highly corrosive.
Last Update：2024-01-02 23:10:35
TRIFLUOROACETIC ACID - Preparation Method
Open Data Verified Data
trifluoroacetic acid can be prepared by oxidation of 3,3, 3-fluoropropene by potassium permanganate, or by reaction of trichloroacetonitrile with hydrogen fluoride to first generate trifluoroacetonitrile, followed by hydrolysis; it can also be prepared by electrochemical fluorination with acetic acid or acetic anhydride.
Last Update：2022-01-01 09:25:17
TRIFLUOROACETIC ACID - Use
Open Data Verified Data
trifluoroacetic acid is an important organic synthesis reagent, from which various fluorine-containing compounds, pesticides and dyes can be synthesized. Trifluoroacetic acid is also a catalyst for esterification and condensation reactions; It can also be used as a protective agent for hydroxyl and amino groups for the synthesis of sugars and polypeptides.
Last Update：2022-01-01 09:25:18
TRIFLUOROACETIC ACID - Safety
Open Data Verified Data
mice were injected intravenously with LD50:1200mg/kg. Inhalation, oral or skin absorption is harmful to the body. Has a strong stimulating effect on the eyes, skin, mucous membranes and respiratory tract.
Last Update：2022-01-01 09:25:18
TRIFLUOROACETIC ACID - Reference Information
| pH range | 1 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | trifluoroacetic acid (TFA molecular formula: CF3COOH) alias trifluoroacetic acid, colorless volatile fuming liquid, odor similar to acetic acid, hygroscopic and irritating odor. Affected by the electron-withdrawing trifluoromethyl group, it is strongly acidic, which is ten thousand times stronger than acetic acid. Melting Point -15.2 °c, boiling point 72.4 °c, density 1.5351g/cm3 (1 °c). It is miscible with water, fluorinated hydrocarbons, methanol, ethanol, diethyl ether, acetone, benzene, carbon tetrachloride and hexane, and can partially dissolve carbon disulfide and more than six carbon alkanes. It is an excellent solvent for proteins and polyesters. It is also an excellent solvent for organic reactions, and can obtain results that are difficult to obtain in general solvents. For example, when quinoline is catalytically hydrogenated in general solvents, the pyridine ring is preferentially hydrogenated, however, the benzene ring is preferentially hydrogenated in trifluoroacetic acid. Trifluoroacetic acid is decomposed into fluorides and carbon dioxide in the presence of aniline. Can be reduced by sodium borohydride or lithium aluminum hydride to trifluoroacetaldehyde and trifluoroethanol. It is stable above 205 ° C., and Ester and amide derivatives are easy to hydrolyze, so that saccharides, amino acids and peptide derivatives can be prepared in the form of acid or anhydride. It is easily dehydrated into trifluoroacetic anhydride by the action of phosphorus pentoxide. Trifluoroacetic acid is an important fat fluorine-containing intermediate. Because of the special structure of trifluoromethyl group, it has different properties from other alcohols, and can participate in a variety of organic synthesis reactions, especially for the synthesis of fluorine-containing pharmaceuticals, pesticides and dyes and other fields, the demand at home and abroad is increasing, and it has become one of the important intermediates of fluorine-containing fine chemicals. |
| pKa | trifluoroacetic acid (TFA). Is a strong carboxylic acid, pKa = 0.23, can stimulate human tissues and skin. Only slight toxicity, but enrichment in non-mobile surface water can affect agricultural and aquatic systems, and TFA undergoes microbial degradation to produce greenhouse gas CHF3. |
| preparation method and production process | trifluoroacetic acid is an important organic synthesis reagent, which can synthesize a variety of fluorine-containing compounds, pesticides and dyes. Trifluoroacetic acid is also a catalyst for esterification and condensation reactions; It can also be used as a protective agent for hydroxyl and amino groups for the synthesis of sugars and polypeptides. Trifluoroacetic acid has a variety of preparation routes: 1, 3,3, 3-trifluoropropene is obtained by potassium permanganate oxidation. 2, acetic acid (or acetyl chloride and acetic anhydride) and hydrofluoric acid, sodium fluoride and other electrochemical fluorination, and then hydrolysis. 1,1,1, 1-trifluoro-2, 3, 3-trichloropropene is obtained by oxidation with potassium permanganate. This raw material can be prepared by Swarts fluorination of hexachloropropene. 4. Prepared by oxidation of 2, 3-dichlorohexafluoro-2-butene. 5. Trifluoroacetonitrile is produced by the reaction of trichloroacetonitrile with hydrogen fluoride and is obtained by hydrolysis. 6, by the oxidation of trifluoro toluene. |
| function and purpose | is mainly used in the production of new pesticides, medicines and dyes, etc, solvent and other fields also have great potential for application and development. Trifluoroacetic acid is mainly used for the synthesis of a variety of herbicides containing trifluoromethyl and heterocyclic, and can synthesize a variety of new herbicides with pyridyl and quinoline groups. As a very strong proton acid, it is widely used in the alkylation of aromatic compounds, as a solvent, trifluoroacetic acid is an excellent solvent for fluorination, nitration and halogenation reactions, especially the excellent protective effect of its derivative trifluoroacetyl group on hydroxyl and amino groups, it has a very important application in the synthesis of amino acids and polypeptide compounds, which is used to remove the tert-butoxycarbonyl (t-boc) protecting group of amino acids in the synthesis of peptides, it can greatly improve the industrial current efficiency of caustic soda and prolong the service life of the membrane. Trifluoroacetic acid can also synthesize trifluoroethanol, trifluoroacetaldehyde and trifluoroacetic anhydride. Mercury trifluoroacetate at room temperature to fluorobenzene Mercury reaction (electrophilic substitution), Hydrazones can also be converted to diazo compounds. The lead salt of this acid can convert aromatic hydrocarbons to phenols. The use of trifluoroacetic acid (TFA) as an ion-pair reagent is a common means in experiments for the separation of polypeptides and proteins by reverse phase chromatography. Trifluoroacetic acid in the mobile phase improves peak shape, overcomes peak spread and tailing problems by interacting with the hydrophobically bonded phase and residual polar surfaces in multiple modes. Trifluoroacetic acid is superior to other ionic modifiers because it is readily volatile and can be conveniently removed from the prepared samples. Trifluoroacetic acid, on the other hand, has a UV maximum absorption of less than 200nm, which interferes little with the detection of the polypeptide at low wavelengths. |
| Application in HPLC | in Reversed-phase chromatographic separation of peptides and proteins, trifluoroacetic acid (TFA) was used as an ion-pair reagent is a common means. Trifluoroacetic acid in the mobile phase improves peak shape, overcomes peak spread and tailing problems by interacting with the hydrophobically bonded phase and residual polar surfaces in multiple modes. Trifluoroacetic acid binds to positive charges and polar groups on the polypeptide to reduce the retention of polarity and brings the polypeptide back to the hydrophobic, inverted surface. In the same manner, the polar surface remaining on the stationary phase was shielded by trifluoroacetic acid. The behavior of trifluoroacetic acid can be understood as its retention on the surface of the reversed phase stationary phase while interacting with the polypeptide and the column bed. Trifluoroacetic acid is superior to other ionic modifiers because it is readily volatile and can be conveniently removed from the prepared samples. Trifluoroacetic acid, on the other hand, has a UV maximum absorption of less than 200nm, which interferes little with the detection of the polypeptide at low wavelengths. By varying the concentration of trifluoroacetic acid, the selectivity of the polypeptide on reverse phase chromatography can be finely adjusted. This effect is very useful for optimizing the separation conditions and increasing the amount of information in complex chromatographic analyses such as fingerprints of polypeptides. The concentration of trifluoroacetic acid in the mobile phase is generally 0.1%, at this concentration, most of the reverse phase chromatography can produce a good peak shape, when the concentration of trifluoroacetic acid is much lower than this level, the broadening and tailing of the peaks becomes apparent. Trifluoroacetic acid in the separation of proteins and other macromolecules when the effect is very good, in actual use, we are difficult to control the concentration of trifluoroacetic acid, because it is volatile substances, if the configuration time is long, it will volatilize some, changing the concentration. After preparation, it must be closed to prevent volatilization. |
| Use | used as pharmaceutical, pesticide intermediates, biochemical reagents, organic Synthesis Reagents The product is a good solvent for many organic compounds, combined with carbon disulfide, can dissolve protein. It is also an excellent solvent for organic reactions. Results that are difficult to obtain in general organic solvents can be obtained. For example, when quinoline is catalytically hydrogenated in a typical solvent, the pyridine ring is preferentially hydrogenated, but the benzene ring is preferentially hydrogenated in trifluoroacetic acid. Trifluoroacetic acid is used in the synthesis of fluorine-containing compounds, pesticides and dyes. It is a catalyst for esterification and condensation reactions; A protective agent for hydroxyl and amino groups, and is used in the synthesis of sugars and polypeptides. It is also used as a mineral dressing agent. as a fine intermediate, it is mainly used for the synthesis of fluorine-containing medicines, pesticides and dyes, and can also be used as raw materials for glass coating process. Is the esterification reaction and condensation reaction catalyst; Hydroxyl and amino protective agent for the synthesis of sugars and peptides used as experimental reagents, solvents, catalyst and used in organic synthesis trifluoroacetylation reagent, polymerization catalyst. Mixed with liquid sulfur dioxide to dissolve proteins. Spectrophotometric analysis. Protein sequence analysis. The use of trifluoroacetic acid (TFA) as an ion-pair reagent is a common means in experiments for the separation of polypeptides and proteins by reverse phase chromatography. Trifluoroacetic acid in the mobile phase improves peak shape, overcomes peak spread and tailing problems by interacting with the hydrophobically bonded phase and residual polar surfaces in multiple modes. Trifluoroacetic acid is superior to other ionic modifiers because it is readily volatile and can be conveniently removed from the prepared samples. Trifluoroacetic acid, on the other hand, has a UV maximum absorption of less than 200nm, which interferes little with the detection of the polypeptide at low wavelengths. Trifluoroacetic acid (TFA) is a good solvent for many organic compounds, such as carbon disulfide in combination, can dissolve proteins. It is also an excellent solvent for organic reactions, and can obtain results that are difficult to obtain in general solvents. For example, when quinoline is catalytically hydrogenated in general solvents, the pyridine ring is preferentially hydrogenated, however, the benzene ring is preferentially hydrogenated in trifluoroacetic acid. Trifluoroacetic acid is decomposed into fluorides and carbon dioxide in the presence of aniline. |
| production method | 1. Preparation by oxidation of 2, 3-dichlorohexafluoro-2-butene; 2.2, 3-dichlorohexafluoro-2-butene is oxidized with fluorine as a catalyst to produce it; 3. Oxidation of 3,3, 3-trifluoropropene by potassium permanganate, or reaction of trichloroacetonitrile with hydrogen fluoride to form trifluoroacetonitrile followed by hydrolysis, or electrochemical fluorination of acetic acid (or acetic anhydride), trifluoroacetic acid can be prepared. |
| category | corrosive article |
| toxicity grade | poisoning |
| Acute toxicity | inhalation-rat LC50:10000 mg/m3; Inhalation-mouse LC50:13500 mg/m3 |
| flammability hazard characteristics | vapor toxic; Flammable; Toxic fluoride smoke from combustion |
| storage and transportation characteristics | The warehouse was ventilated and dried at low temperature; With H pore forming agent, alkali, separate storage of cyanide |
| extinguishing agent | dry sand, dry stone powder, carbon dioxide |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:55:45
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TRIFLUOROACETIC ACID
c.i.pigmentwhite3
三氟丙烯酸甲酯
((1 1-DIMETHYL-2-PENTYNYL)OXY)TRIMETHYL&
环丙烷甲酸, 1-氨基-2-乙烯基-, 乙基 酯
5ml流式管(带盖,非无菌)
Ethyl p-aminobenzoate
Z-VAINE NCA[FOR VALGANCICLOVIR]
c.i.pigmentwhite3
三氟丙烯酸甲酯
((1 1-DIMETHYL-2-PENTYNYL)OXY)TRIMETHYL&
环丙烷甲酸, 1-氨基-2-乙烯基-, 乙基 酯
5ml流式管(带盖,非无菌)
Ethyl p-aminobenzoate
Z-VAINE NCA[FOR VALGANCICLOVIR]
Raw Materials for TRIFLUOROACETIC ACID
Downstream Products for TRIFLUOROACETIC ACID