Difference between revisions of "Trifluoroacetic acid"
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| OtherNames = 2,2,2-Trifluoroacetic acid<br>2,2,2-Trifluoroethanoic acid<br>Perfluoroacetic acid<br>Trifluoroethanoic acid<br>TFA | | OtherNames = 2,2,2-Trifluoroacetic acid<br>2,2,2-Trifluoroethanoic acid<br>Perfluoroacetic acid<br>Trifluoroethanoic acid<br>TFA | ||
<!-- Images --> | <!-- Images --> | ||
| − | | ImageFile = | + | | ImageFile = Trifluoroacetic acid structural formula.png |
| ImageSize = | | ImageSize = | ||
| ImageAlt = | | ImageAlt = | ||
| Line 43: | Line 43: | ||
| 3DMet = | | 3DMet = | ||
| Abbreviations = | | Abbreviations = | ||
| − | | SMILES = | + | | SMILES = C(=O)(C(F)(F)F)O |
}} | }} | ||
| Section2 = {{Chembox Properties | | Section2 = {{Chembox Properties | ||
| AtmosphericOHRateConstant = | | AtmosphericOHRateConstant = | ||
| − | | Appearance = Colorless liquid | + | | Appearance = Colorless fuming liquid |
| BoilingPt = | | BoilingPt = | ||
| BoilingPtC = 72.4 | | BoilingPtC = 72.4 | ||
| Line 64: | Line 64: | ||
| pKa = 0.23 | | pKa = 0.23 | ||
| pKb = | | pKb = | ||
| − | | Solubility = | + | | Solubility = Miscible |
| − | | SolubleOther = [[acetone]], [[benzene]], [[carbon tetrachloride]], [[diethyl ether]], [[ethanol]], [[hexane]] | + | | SolubleOther = Reacts with alkali, amines<br>Miscible with [[acetone]], [[benzene]], [[carbon tetrachloride]], [[diethyl ether]], [[ethanol]], [[hexane]] |
| Solvent = | | Solvent = | ||
| VaporPressure = 82.5 mmHg (20 °C) | | VaporPressure = 82.5 mmHg (20 °C) | ||
| Line 88: | Line 88: | ||
}} | }} | ||
| Section6 = {{Chembox Hazards | | Section6 = {{Chembox Hazards | ||
| − | | AutoignitionPt = | + | | AutoignitionPt = Non-flammable |
| ExploLimits = | | ExploLimits = | ||
| ExternalMSDS = [https://www.docdroid.net/1q4CkSO/trifluoroacetic-acid-sa.pdf.html Sigma-Aldrich] | | ExternalMSDS = [https://www.docdroid.net/1q4CkSO/trifluoroacetic-acid-sa.pdf.html Sigma-Aldrich] | ||
| − | | FlashPt = | + | | FlashPt = Non-flammable |
| LD50 = 200 mg/kg (rat, oral) | | LD50 = 200 mg/kg (rat, oral) | ||
| LC50 = | | LC50 = | ||
| Line 105: | Line 105: | ||
| OtherFunction = | | OtherFunction = | ||
| OtherFunction_label = | | OtherFunction_label = | ||
| − | | OtherCompounds = [[Acetic acid]] | + | | OtherCompounds = [[Acetic acid]]<br>[[Fluoroacetic acid]]<br>[[Difluoroacetic acid]] |
}} | }} | ||
}} | }} | ||
| − | '''Trifluoroacetic acid''' is an organofluorine compound, an organic acid with the formula '''CF<sub>3</sub>COOH'''. TFA is an analogue of [[acetic acid]], with the three hydrogen atoms replaced by three [[fluorine]] atoms. The acidity of TFA is approximately 34,000 times stronger than that of acetic acid due to the electronegativity of the trifluoromethyl group. | + | '''Trifluoroacetic acid''' ('''TFA''') is an organofluorine compound, an organic acid with the formula '''CF<sub>3</sub>COOH'''. TFA is an analogue of [[acetic acid]], with the three hydrogen atoms replaced by three [[fluorine]] atoms. The acidity of TFA is approximately 34,000 times stronger than that of acetic acid due to the electronegativity of the trifluoromethyl group. |
==Properties== | ==Properties== | ||
| Line 115: | Line 115: | ||
:CF<sub>3</sub>COOH + MOH → CF<sub>3</sub>COOM + H<sub>2</sub>O | :CF<sub>3</sub>COOH + MOH → CF<sub>3</sub>COOM + H<sub>2</sub>O | ||
| + | |||
| + | Decarboxylation of trifluoroacetic acid yields fluoroform.<ref>Kirschner, E., Chemical and Engineering News 1994, p. 8</ref> | ||
===Physical=== | ===Physical=== | ||
| − | Trifluoroacetic acid is a colorless volatile liquid, with a strong pungent acetic smell. It is miscible with water and organic solvents. | + | Trifluoroacetic acid is a colorless volatile liquid, which fumes in open air, with a strong pungent acetic smell. It reacts with bases and amines, and it is miscible with [[water]] and a variety of organic solvents, like alcohols and ethers. |
==Availability== | ==Availability== | ||
| − | TFA is sold by various chemical suppliers. | + | TFA is sold by various chemical suppliers, but it's not cheap. |
==Preparation== | ==Preparation== | ||
| Line 133: | Line 135: | ||
==Projects== | ==Projects== | ||
| + | *Removal of nitrogen and oxygen protecting groups in organic chemistry | ||
*Make [http://www.sciencemadness.org/talk/viewthread.php?tid=16611 copper (II) trifluoroacetate] | *Make [http://www.sciencemadness.org/talk/viewthread.php?tid=16611 copper (II) trifluoroacetate] | ||
*Make trifluoroacetic anhydride | *Make trifluoroacetic anhydride | ||
*Make 2,2,2-trifluoroethanol | *Make 2,2,2-trifluoroethanol | ||
*Make holmium trifluoroacetate | *Make holmium trifluoroacetate | ||
| + | *Compound collecting | ||
==Handling== | ==Handling== | ||
===Safety=== | ===Safety=== | ||
| − | TFA is corrosive and should be handled with proper protection, in well ventilated areas. | + | TFA is volatile and corrosive and should be handled with proper protection, in well ventilated areas. |
===Storage=== | ===Storage=== | ||
| Line 161: | Line 165: | ||
[[Category:Organofluorine compounds]] | [[Category:Organofluorine compounds]] | ||
[[Category:Acids]] | [[Category:Acids]] | ||
| − | [[Category: | + | [[Category:Strong acids]] |
[[Category:Carboxylic acids]] | [[Category:Carboxylic acids]] | ||
[[Category:Solvents]] | [[Category:Solvents]] | ||
| Line 168: | Line 172: | ||
[[Category:Volatile chemicals]] | [[Category:Volatile chemicals]] | ||
[[Category:Liquids]] | [[Category:Liquids]] | ||
| + | [[Category:Irritants]] | ||
Latest revision as of 18:09, 30 July 2024
| |
| Names | |
|---|---|
| IUPAC name
Trifluoroacetic acid
| |
| Preferred IUPAC name
Trifluoroacetic acid | |
| Other names
2,2,2-Trifluoroacetic acid
2,2,2-Trifluoroethanoic acid Perfluoroacetic acid Trifluoroethanoic acid TFA | |
| Identifiers | |
| Jmol-3D images | Image |
| |
| Properties | |
| C2HF3O2 CF3COOH | |
| Molar mass | 114.02 g/mol |
| Appearance | Colorless fuming liquid |
| Odor | Strong pungent odor |
| Density | 1.531 g/cm3 (20 °C) 1.489 g/cm3 (25 °C) |
| Melting point | −15.4 °C (4.3 °F; 257.8 K) |
| Boiling point | 72.4 °C (162.3 °F; 345.5 K) |
| Miscible | |
| Solubility | Reacts with alkali, amines Miscible with acetone, benzene, carbon tetrachloride, diethyl ether, ethanol, hexane |
| Vapor pressure | 82.5 mmHg (20 °C) |
| Acidity (pKa) | 0.23 |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | Non-flammable |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
200 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Acetic acid Fluoroacetic acid Difluoroacetic acid |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Trifluoroacetic acid (TFA) is an organofluorine compound, an organic acid with the formula CF3COOH. TFA is an analogue of acetic acid, with the three hydrogen atoms replaced by three fluorine atoms. The acidity of TFA is approximately 34,000 times stronger than that of acetic acid due to the electronegativity of the trifluoromethyl group.
Contents
Properties
Chemical
Trifluoroacetic acid reacts with bases to form trifluoroacetate salts.
- CF3COOH + MOH → CF3COOM + H2O
Decarboxylation of trifluoroacetic acid yields fluoroform.[1]
Physical
Trifluoroacetic acid is a colorless volatile liquid, which fumes in open air, with a strong pungent acetic smell. It reacts with bases and amines, and it is miscible with water and a variety of organic solvents, like alcohols and ethers.
Availability
TFA is sold by various chemical suppliers, but it's not cheap.
Preparation
TFA can be synthesized by the electrofluorination of acetyl chloride and acetic anhydride, followed by hydrolysis of the resulting trifluoroacetyl fluoride:
- CH3COCl + 4 HF → CF3COF + 3 H2 + HCl
- CF3COF + H2O → CF3COOH + HF
An older route to TFA involves the oxidation of 1,1,1-trifluoro-2,3,3-trichloropropene with potassium permanganate, the latter being prepared by Swarts fluorination of hexachloropropene.
Oxidation of 1,1,1-trifluoroethane aka R-143a, a freon commonly used as refrigerent and propellant in canned air products will also yield TFA. The oxidation is done by mixing R-143a with air and passing the mixture through an electric discharge of 15,000 V. Water vapor is used as carrying medium, which also helps preventing the degradation of TFA and unreacted R-143a.[2]
Projects
- Removal of nitrogen and oxygen protecting groups in organic chemistry
- Make copper (II) trifluoroacetate
- Make trifluoroacetic anhydride
- Make 2,2,2-trifluoroethanol
- Make holmium trifluoroacetate
- Compound collecting
Handling
Safety
TFA is volatile and corrosive and should be handled with proper protection, in well ventilated areas.
Storage
Trifluoroacetic acid should be kept in closed bottles, away from heat and light, in a corrosive acid cabinet. Don't store it near ammonia or other volatile chemicals.
Disposal
Trifluoroacetic acid can be neutralized with a base. Trifluoroacetates have low toxicity and generally do not require special disposal.
References
- ↑ Kirschner, E., Chemical and Engineering News 1994, p. 8
- ↑ http://pubs.acs.org/doi/abs/10.1021/jo01062a068
Relevant Sciencemadness threads
- Chemical pages without CAS Registry Number
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Articles containing unverified chemical infoboxes
- Chemical compounds
- Organic compounds
- Fluorine compounds
- Organofluorine compounds
- Acids
- Strong acids
- Carboxylic acids
- Solvents
- Polar solvents
- Protic solvents
- Volatile chemicals
- Liquids
- Irritants
