Sodium trifluoroacetate

Last updated
Sodium trifluoroacetate
Sodium trifluoroacetate.svg
Sample of sodium trifluoroacetate.jpg
Names
IUPAC name
Sodium trifluoroacetate
Other names
Sodium perfluoroacetate
Sodium 2,2,2-trifluoroacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.982 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 220-879-6
PubChem CID
UNII
  • Key: UYCAUPASBSROMS-UHFFFAOYSA-M
  • InChI=1S/C2HF3O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1
  • C(C(=O)[O-])(F)(F)F.[Na+]
Properties
C2F3NaO2
Molar mass 136.005 g·mol−1
AppearanceWhite crystalline powder
Density 1.49 g mL−1
Melting point 207 °C (405 °F; 480 K)
Boiling point Decomposes
625 g/L
Solubility soluble in alcohol, acetonitrile, dimethylformamide and most of polar organic solvents
Acidity (pKa)0.23 (conjugate acid)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, Irritant, Harmful to environment
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Danger
H300, H315, H319, H335, H410
P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
0
1
Flash point Non-flammable
Non-flammable
Related compounds
Other anions
Sodium trichloroacetate
Other cations
Lithium trifluoroacetate
Potassium trifluoroacetate
Related compounds
Sodium formate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sodium trifluoroacetate is a chemical compound with a formula of CF3CO2Na. It is the sodium salt of trifluoroacetic acid. It is used as a source of trifluoromethylations. [1]

Contents

Basicity

With a pKa of 0.23 for trifluoroacetic acid, the trifluoroacetate ion is an extremely weak base compared to acetic acid, which has a pKa of 4.76. This is due to the electron-withdrawing effect of the three fluorine atoms adjacent the carboxylate group. Strong acids such as hydrochloric acid or sulfuric acid can protonate the trifluoroacetate ion to trifluoroacetic acid:

In general, trifluoroacetate reacts in equilibrium with hydronium cations to form trifluoroacetic acid:

The general reaction with hydronium is in equilibrium due to the similarity in pKa between trifluoroacetic acid and the hydronium ion.

Preparation

One convenient method is by dissolving an equivalent amount of sodium carbonate in 50% aqueous solution of trifluoroacetic acid. The solution is filtered and evaporated by vacuum evaporation (with special care to avoid decomposition of the salt by overheating). The solid obtained is dried under vacuum at 100 °C. [2]

Uses

Sodium trifluoroacetate is a useful reagent for trifluoromethylation.

The trifluoromethylation process with sodium trifluoroacetate. Trifluoromethylation with sodium trifluoroacetate.gif
The trifluoromethylation process with sodium trifluoroacetate.

See also

Related Research Articles

<span class="mw-page-title-main">Acid</span> Chemical compound giving a proton or accepting an electron pair

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid.

<span class="mw-page-title-main">Acid–base reaction</span> Chemical reaction between an acid and a base

In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.

In chemistry, an acid dissociation constant is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction

Solubility equilibrium is a type of dynamic equilibrium that exists when a chemical compound in the solid state is in chemical equilibrium with a solution of that compound. The solid may dissolve unchanged, with dissociation, or with chemical reaction with another constituent of the solution, such as acid or alkali. Each solubility equilibrium is characterized by a temperature-dependent solubility product which functions like an equilibrium constant. Solubility equilibria are important in pharmaceutical, environmental and many other scenarios.

<span class="mw-page-title-main">Ammonium</span> Chemical compound

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups.

<span class="mw-page-title-main">Base (chemistry)</span> Type of chemical substance

In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century.

In chemistry, an amphoteric compound is a molecule or ion that can react both as an acid and as a base. What exactly this can mean depends on which definitions of acids and bases are being used.

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<span class="mw-page-title-main">Neutralization (chemistry)</span> Chemical reaction in which an acid and a base react quantitatively

In chemistry, neutralization or neutralisation is a chemical reaction in which acid and a base react with an equivalent quantity of each other. In a reaction in water, neutralization results in there being no excess of hydrogen or hydroxide ions present in the solution. The pH of the neutralized solution depends on the acid strength of the reactants.

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<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

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<span class="mw-page-title-main">Dissociation (chemistry)</span> Separation of molecules or ionic compounds into smaller constituent entities

Dissociation in chemistry is a general process in which molecules (or ionic compounds such as salts, or complexes) separate or split into other things such as atoms, ions, or radicals, usually in a reversible manner. For instance, when an acid dissolves in water, a covalent bond between an electronegative atom and a hydrogen atom is broken by heterolytic fission, which gives a proton (H+) and a negative ion. Dissociation is the opposite of association or recombination.

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<span class="mw-page-title-main">Trifluoroacetic acid</span> Chemical compound

Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor.

<span class="mw-page-title-main">Triflic acid</span> Chemical compound

Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.

<span class="mw-page-title-main">Hydrochloric acid</span> Aqueous solution of hydrogen chloride

Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid. It is a component of the gastric acid in the digestive systems of most animal species, including humans. Hydrochloric acid is an important laboratory reagent and industrial chemical.

Acid strength is the tendency of an acid, symbolised by the chemical formula , to dissociate into a proton, , and an anion, . The dissociation of a strong acid in solution is effectively complete, except in its most concentrated solutions.

References

  1. Chang, Ying; Cai, Chun (June 2005). "Trifluoromethylation of carbonyl compounds with sodium trifluoroacetate". Journal of Fluorine Chemistry. 126 (6): 937–940. doi:10.1016/j.jfluchem.2005.04.012.
  2. Prakash, G. K. Surya; Mathew, Thomas (2010), "Sodium Trifluoroacetate", Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289x.rn01136, ISBN   9780470842898