Information about Trifluoroacetic Acid
| Trifluoroacetic acid | |
|---|---|
) ) ) | |
| General | |
| Systematic name | Trifluoroacetic acid |
| Other names | Perfluoroacetic acid Trifluoroethanoic acid TFA |
| Molecular formula | C2HF3O2 |
| SMILES | FC(F)(F)C(O)=O |
| Molar mass | 114.03 g/mol |
| Appearance | colorless liquid |
| CAS number | [76-05-1] |
| Properties | |
| Density and phase | 1.5351 g/cm3, 20 °C |
| Solubility in water | miscible |
| Melting point | -15.4 °C; 257.75 K |
| Boiling point | 72.4 °C; 345.55 K |
| Acidity (pKa) | 0.3 |
| Viscosity | ? cP at ? °C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Highly corrosive |
| NFPA 704 | ) 1 3 1 |
| Flash point | -3 °C |
| R/S statement | R: R20 R35 R52/53 S: S9 S26 S27 S28 S45 S61 |
| RTECS number | AJ9625000 |
| Related compounds | |
| Related compounds | Acetic acid Trichloroacetic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Trifluoroacetic acid (TFA) is the chemical compound with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the three very electronegative fluorine atoms. Relative to acetic acid, TFA is almost 100,000-fold more acidic. TFA is widely used in organic chemistry.
Uses
TFA is a reagent used frequently in organic synthesis because of a combination of convenient properties: volatility, solubility in organic solvents, and its strength.[1] It is also less oxidizing than sulfuric acid but more readily available in anhydrous form than hydrochloric acid. One complication to its use is that TFA forms an azeotrope with water with a boiling point of 105 °C.It is also frequently used as a buffer in liquid chromatography for separation of organic compounds, particularly peptides and small proteins. It is a versatile solvent for NMR spectroscopy.
The derived acid anhydride, [CF3C(O)]2O, is a common reagent for introducing the trifluoracetyl group.
Synthesis
Electrofluorination of acetic acid with the Simons method is the best way to obtain trifluoroacetic acid. The anodic reaction of the electrolysis of a mixture of hydrogen fluoride and acetic acid below the voltage at which elemental fluorine (F2) develops is a mild reaction which leaves the carboxylic group intact.References
1. ^ Eidman, K. F.; Nichols, P. J. "Trifluoroacetic Acid" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Water (H2O, HOH) is the most abundant molecule on Earth's surface, composing of about 70% of the Earth's surface as liquid and solid state in addition to being found in the atmosphere as a vapor.
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. According to the Brønsted-Lowry theory of acids and bases an acid is only recognised by its reaction with a base.
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Viscosity is a measure of the resistance of a fluid to deform under either shear stress or extensional stress. It is commonly perceived as "thickness", or resistance to flow.
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The poise (symbol P; IPA: /pwɑːz/) is the unit of dynamic viscosity in the centimetre gram second system of units. It is named after Jean Louis Marie Poiseuille.
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material safety data sheet (MSDS) is a form containing data regarding the properties of a particular substance. An important component of product stewardship and workplace safety, it is intended to provide workers and emergency personnel with procedures for handling or
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Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. Its structural formula is represented as CH3COOH.
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Trichloroacetic acid (also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. It is a strong acid, comparable to sulfuric acid.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted acids — they are proton donors.
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Electronegativity, symbol χ, is a chemical property which describes the power of an atom (or, more rarely, a functional group) to attract electrons towards itself.[1] First proposed by Linus Pauling in 1932 as a development of valence bond theory,[2]
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100% F is stable with 10 neutrons
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Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. Its structural formula is represented as CH3COOH.
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Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may
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