Sodium trifluoroacetate

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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:

CF3CO2 + HCl → CF3CO2H + Cl
CF3CO2 + H2SO4 → CF3CO2H + HSO4

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

CF3CO2 + H3O+CF3CO2H + H2O

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.

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

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

Hydroxide is a diatomic anion with chemical formula OH. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate in aqueous solution, liberating solvated hydroxide ions. Sodium hydroxide is a multi-million-ton per annum commodity chemical. The corresponding electrically neutral compound HO is the hydroxyl radical. The corresponding covalently bound group –OH of atoms is the hydroxy group. Both the hydroxide ion and hydroxy group are nucleophiles and can act as catalysts in organic chemistry.

Hydrolysis is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.

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<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.

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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.

<span class="mw-page-title-main">Chromate and dichromate</span> Chromium(VI) anions

Chromate salts contain the chromate anion, CrO2−
4
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2
O2−
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<span class="mw-page-title-main">Lithium diisopropylamide</span> Chemical compound

Lithium diisopropylamide is a chemical compound with the molecular formula LiN(CH 2)2. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.

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

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

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<span class="mw-page-title-main">Diazonium compound</span> Group of organonitrogen compounds

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N+≡N]X where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent compound where R is hydrogen, is diazenylium.

<span class="mw-page-title-main">Trifluoroacetic acid</span> One of the lightest perfluoro compounds

Trifluoroacetic acid (TFA) is a synthetic organofluorine compound with the chemical formula CF3CO2H. It is a haloacetic acid, with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms. It is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, Ka, that is approximately 34,000 times higher, as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. TFA is commonly used in organic chemistry for various purposes.

Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib, and triflurazin. A relevant agrochemical is trifluralin. The development of synthetic methods for adding trifluoromethyl groups to chemical compounds is actively pursued in academic research.

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

Cerium nitrate refers to a family of nitrates of cerium in the +3 or +4 oxidation state. Often these compounds contain water, hydroxide, or hydronium ions in addition to cerium and nitrate. Double nitrates of cerium also exist.

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

Ethyl trifluoroacetate is a chemical compound from the trifluoroacetate group.

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