Sodium 2,2,2-trifluoroacetate"},"Section1":{"wt":"{{Chembox Identifiers\n| CASNo = 2923-18-4\n| UNII = 255JUV5YVI\n| PubChem = 517019\n| EC_number = 220-879-6\n| ChemSpiderID = 68703\n| InChI=1S/C2HF3O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1\n| StdInChIKey = UYCAUPASBSROMS-UHFFFAOYSA-M\n| SMILES = C(C(=O)[O-])(F)(F)F.[Na+]\n}}"},"Section2":{"wt":"{{Chembox Properties\n| C=2 | F=3 | O=2 | Na=1\n| Appearance = White crystalline powder\n| Density = 1.49 g mL−1\n| MeltingPtC = 207\n| BoilingPt = Decomposes \n| pKa = 0.23 (conjugate acid)\n| Solubility = 625 g/L\n| SolubleOther = soluble in [[ethanol|alcohol]],[[acetonitrile]],[[dimethylformamide]] and most of polar [[organic solvents]]\n}}"},"Section7":{"wt":"{{Chembox Hazards\n| MainHazards = Toxic,Irritant,Harmful to environment\n| NFPA-H = 2\n| NFPA-F = 0\n| NFPA-R = 1\n| NFPA-S = \n| FlashPt = Non-flammable\n| AutoignitionPt = Non-flammable\n| GHSPictograms ={{GHS06}}{{GHS07}}{{GHS09}}\n| GHSSignalWord = Danger\n| HPhrases ={{H-phrases|300|315|319|335|410}}\n| PPhrases ={{P-phrases|261|264|270|271|273|280|301+310|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|391|403+233|405|501}}\n}}"},"Section9":{"wt":"{{Chembox Related\n| OtherCations = [[Lithium trifluoroacetate]]
[[Potassium trifluoroacetate]]\n| OtherAnions = [[Sodium trichloroacetate]]\n| OtherCompounds = [[Sodium formate]]\n}}"}},"i":0}}]}" id="mwBA">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}
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Names | |
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IUPAC name Sodium trifluoroacetate | |
Other names Sodium perfluoroacetate Sodium 2,2,2-trifluoroacetate | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.018.982 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C2F3NaO2 | |
Molar mass | 136.005 g·mol−1 |
Appearance | White 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: | |
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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) | |
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]
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.
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]
Sodium trifluoroacetate is a useful reagent for trifluoromethylation.
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.
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 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.
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.
A buffer solution is a solution where the pH does not change significantly on dilution or if an acid or base is added at constant temperature. Its pH changes very little when a small amount of strong acid or base is added to it. Buffer solutions are used as a means of keeping pH at a nearly constant value in a wide variety of chemical applications. In nature, there are many living systems that use buffering for pH regulation. For example, the bicarbonate buffering system is used to regulate the pH of blood, and bicarbonate also acts as a buffer in the ocean.
In chemistry, hydronium is the cation [H3O]+, also written as H3O+, the type of oxonium ion produced by protonation of water. It is often viewed as the positive ion present when an Arrhenius acid is dissolved in water, as Arrhenius acid molecules in solution give up a proton to the surrounding water molecules. In fact, acids must be surrounded by more than a single water molecule in order to ionize, yielding aqueous H+ and conjugate base.
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, the common-ion effect refers to the decrease in solubility of an ionic precipitate by the addition to the solution of a soluble compound with an ion in common with the precipitate. This behaviour is a consequence of Le Chatelier's principle for the equilibrium reaction of the ionic association/dissociation. The effect is commonly seen as an effect on the solubility of salts and other weak electrolytes. Adding an additional amount of one of the ions of the salt generally leads to increased precipitation of the salt, which reduces the concentration of both ions of the salt until the solubility equilibrium is reached. The effect is based on the fact that both the original salt and the other added chemical have one ion in common with each other.
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction. The species formed is the conjugate base of that acid. The complementary process, when a proton is added (transferred) to a Brønsted–Lowry base, is protonation (or hydronation). The species formed is the conjugate acid of that base.
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.
Chromate salts contain the chromate anion, CrO2−
4. Dichromate salts contain the dichromate anion, Cr
2O2−
7. They are oxyanions of chromium in the +6 oxidation state and are moderately strong oxidizing agents. In an aqueous solution, chromate and dichromate ions can be interconvertible.
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.
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.
Acid salts are a class of salts that produce an acidic solution after being dissolved in a solvent. Its formation as a substance has a greater electrical conductivity than that of the pure solvent. An acidic solution formed by acid salt is made during partial neutralization of diprotic or polyprotic acids. A half-neutralization occurs due to the remaining of replaceable hydrogen atoms from the partial dissociation of weak acids that have not been reacted with hydroxide ions to create water molecules.
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.
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.
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.
Ethyl trifluoroacetate is a chemical compound from the trifluoroacetate group.