Trifluoroacetyl chloride

Last updated
Trifluoroacetyl chloride
Trifluoroacetyl chloride skeletal.svg
Trifluoroacetyl chloride Ball and Stick.png
Trifluoroacetyl chloride Space Fill.png
Names
Preferred IUPAC name
Trifluoroacetyl chloride
Other names
2,2,2-Trifluoroacetyl chloride
Identifiers
3D model (JSmol)
1098994
ChEBI
ChemSpider
ECHA InfoCard 100.005.961 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-556-2
PubChem CID
UNII
UN number 3057
  • InChI=1S/C2ClF3O/c3-1(7)2(4,5)6
    Key: PNQBEPDZQUOCNY-UHFFFAOYSA-N
  • InChI=1/C2ClF3O/c3-1(7)2(4,5)6
    Key: PNQBEPDZQUOCNY-UHFFFAOYAG
  • C(=O)(C(F)(F)F)Cl
Properties
C2ClF3O
Molar mass 132.469
Melting point −146 °C (−231 °F; 127 K)
Boiling point −27 °C (−17 °F; 246 K)
Hazards
GHS labelling:
GHS-pictogram-bottle.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H312, H314, H330, H335, H412
P260, P261, P264, P271, P273, P280, P284, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Trifluoroacetyl chloride (also known as TFAC [1] ) is a toxic gaseous chemical compound with the chemical formula C 2 Cl F 3O. [2] [3] TFAC is the perfluorinated version of acetyl chloride. The compound is a gas, but it is usually shipped as a liquid under high pressure. [3]

Contents

Properties

Trifluoroacetyl chloride has a vapor density that is 4.6 times that of air, or about 1.384 grams per milliliter at 20 °C (68 °F) as a liquid under pressure. [1] [2] The compound has a melting point of −146 °C (−231 °F) and a boiling point of −27 °C (−17 °F). [2] The compound easily reacts with water and moist air to produce the toxic gas hydrogen chloride and trifluoroacetic acid. [3] [4]

Trifluoroacetyl chloride is incompatible with a number of other varieties of chemicals, such as amines, alcohols, alkalis, and strong oxidizers. It reacts strongly with amines and alkalis. It also reacts violently with diisopropyl ether, or any ether if metal salts are present, sometimes causing an explosion. [3]

Trifluoroacetyl chloride's heat of vaporization is 20 kilojoules per mole at 65 btus per pound. [1]

Numerous atoms and compounds can replace the chlorine atom in trifluoroacetyl chloride. These include iodine, fluorine, cyanide, thiocyanate, and isocyanate. The compound also reacts easily with metal alkyls. This reaction has the form of CF3COCl + MR → CF3COR + MCl, where M can be lithium, copper, magnesium, mercury, silver, or cadmium. When trifluoroacetyl chloride also reacts with ketene and esterification yields occur, the resulting reaction forms trifluoroacetoacetate esters. [1]

Trifluoroacetyl chloride also reacts with soil, cellulose-based absorbents, and clay-based absorbents. [5] When the compound reacts with water in contact with metal, hydrogen gas, which is explosive, is produced. [6] The compound forms a clustering reaction with a methyl group (CH3). [7]

Production

Trifluoroacetyl chloride can be produced by catalytic chlorination of chlorine and trifluoroacetaldehyde. [8] The compound can also be produced if halothane is oxidized using CYP2E1. [9] This is also done with CYP2A6 instead of CPY2E1, but less readily. [10]

Applications and storage

Trifluoroacetyl chloride's applications include uses in medicine, pesticides, the fine chemical industry, and the organic intermediate industry. [3] However, the compound itself is not sold to consumers or as a commodity. [4] Some acetoacetic esters produced by trifluoroacetyl chloride are in turn used to perform chemical reactions that result in the formation of compounds with agricultural and pharmaceutical applications. [1]

One of trifluoroacetyl chloride's uses is in adding trifluoromethyl to complex molecules during chemical reactions. [1]

In the late 1970s, trifluoroacetyl chloride was explored for use as a reagent for nuclear magnetic resonance. It was intended to be used on amines, alcohols, thiols, and phenols. [11]

Trifluoroacetyl chloride is typically stored as a liquid under high pressure. [4]

Biological role, precautions, and toxicity

Liquid trifluoroacetyl chloride can cause frostbite if it comes in contact with unprotected skin. If inhaled, the compound in its gaseous state will irritate the eyes, skin, and mucous membranes. Trifluoroacetyl chloride is a toxic compound, and may be fatal if inhaled, ingested or absorbed through the skin. [12] When the compound burns, it produces toxic gases. [3] It also corrodes the respiratory tract. [4] The compound is also a lacrimator. It can cause dyspnea if inhaled by mice, rats, or guinea pigs. A concentration of 35.3 parts per million of trifluoroacetyl chloride is enough to usually kill a rat in six hours. [6]

Trifluoroacetyl chloride does not bioaccumulate significantly. However, it is harmful to aquatic organisms. [13]

Trifluoroacetyl chloride is metabolized by Cytochrome P450 enzymes. The immune systems of organisms typically react to this. [14]

See also

Related Research Articles

<span class="mw-page-title-main">Chlorine</span> Chemical element, symbol Cl and atomic number 17

Chlorine is a chemical element; it has symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

<span class="mw-page-title-main">Halogen</span> Group of chemical elements

The halogens are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the radioactive elements astatine (At) and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group 17.

<span class="mw-page-title-main">Phosgene</span> Toxic gaseous compound (COCl2)

Phosgene is an organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite is an alkaline inorganic chemical compound with the formula NaOCl. It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of sodium cations and hypochlorite anions.

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

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Solvent, now banned for ozone depletion

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. A colourless and sweet-smelling liquid, it was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and as such use has declined since 1996. Trichloroethane should not be confused with the similar-sounding trichloroethene which is also commonly used as a solvent.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

In chemistry, an interhalogen compound is a molecule which contains two or more different halogen atoms and no atoms of elements from any other group.

Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

Chlorine trifluoride is an interhalogen compound with the formula ClF3. It is a colorless, poisonous, corrosive, and extremely reactive gas that condenses to a pale-greenish yellow liquid, the form in which it is most often sold. It is famous for its extreme oxidation properties. The compound is primarily of interest in plasmaless cleaning and etching operations in the semiconductor industry, in nuclear reactor fuel processing, historically as a component in rocket fuels, and various other industrial operations owing to its corrosive nature.

<span class="mw-page-title-main">Hydrazoic acid</span> Unstable and toxic chemical compound

Hydrazoic acid, also known as hydrogen azide, azic acid or azoimide, is a compound with the chemical formula HN3. It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. The oxidation state of the nitrogen atoms in hydrazoic acid is fractional and is -1/3. It was first isolated in 1890 by Theodor Curtius. The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes.

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

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

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

Disulfur decafluoride is a chemical compound with the formula S2F10. It was discovered in 1934 by Denbigh and Whytlaw-Gray. Each sulfur atom of the S2F10 molecule is octahedral, and surrounded by five fluorine atoms and one sulfur atom. The two sulfur atoms are connected by a single bond. In the S2F10 molecule, the oxidation state of each sulfur atoms is +5, but their valency is 6. S2F10 is highly toxic, with toxicity four times that of phosgene.

Perchloryl fluoride is a reactive gas with the chemical formula ClO
3F. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

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

Chromyl fluoride is an inorganic compound with the formula CrO2F2. It is a violet-red colored crystalline solid that melts to an orange-red liquid.

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

Thiophosphoryl fluoride is an inorganic molecular gas with formula PSF3 containing phosphorus, sulfur and fluorine. It spontaneously ignites in air and burns with a cool flame. The discoverers were able to have flames around their hands without discomfort, and called it "probably one of the coldest flames known". The gas was discovered in 1888.

Potassium hypochlorite is a chemical compound with the chemical formula KOCl, also written as KClO. It is the potassium salt of hypochlorous acid. It consists of potassium cations and hypochlorite anions. It is used in variable concentrations, often diluted in water solution. Its aqueous solutions are colorless liquids that have a strong chlorine smell. It is used as a biocide and disinfectant.

<span class="mw-page-title-main">Chlorine-releasing compounds</span>

Chlorine-releasing compounds, also known as chlorine base compounds, is jargon to describe certain chlorine-containing substances that are used as disinfectants and bleaches. They include the following chemicals: sodium hypochlorite, chloramine, halazone, and sodium dichloroisocyanurate. They are widely used to disinfect water and medical equipment, and surface areas as well as bleaching materials such as cloth. The presence of organic matter can make them less effective as disinfectants. They come as a liquid solution, or as a powder that is mixed with water before use.

References

  1. 1 2 3 4 5 6 Trifluoroacetyl Chloride (PDF), retrieved October 14, 2013
  2. 1 2 3 Trifluoroacetyl chloride, 2013, retrieved October 10, 2013
  3. 1 2 3 4 5 6 TRIFLUOROACETYL CHLORIDE, 2010, retrieved October 10, 2013
  4. 1 2 3 4 December 2011 Product Safety Summary of Trifluoroacetyl chloride (TFAC) (PDF), December 2011, retrieved October 14, 2013
  5. ↑ TRIFLUOROACETYL CHLORIDE , retrieved October 16, 2013
  6. 1 2 Trifluoroacetyl chloride, National Institutes of Health, August 2013, retrieved October 18, 2013
  7. ↑ Trifluoroacetyl chloride, NIST, 2011, retrieved October 21, 2013
  8. ↑ Bernard Cheminal; Henri Mathais; Marc Thomarat (February 17, 1987), Process for preparing trifluoroacetyl chloride , retrieved October 18, 2013
  9. ↑ Arthur J. Atkinson, Jr.; Shiew-Mei Huang; Juan J.L. Lertora; Sanford P. Markey, eds. (September 18, 2012), Principles of Clinical Pharmacology, Academic Press, ISBN   9780123854728 , retrieved October 22, 2013
  10. ↑ Current Concepts in Drug Metabolism and Toxicology, Academic Press, November 27, 2012, ISBN   9780123983596 , retrieved October 22, 2013
  11. ↑ P. Sleevi; T.E. Glass; H.C. Dorn (October 1979), "Trifluoroacetyl chloride for characterization of organic functional groups by fluorine-19 nuclear magnetic resonance spectrometry", Analytical Chemistry, 51 (12): 1931–1934, doi:10.1021/ac50048a009
  12. ↑ "Trifluoroacetyl chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-02.
  13. ↑ Solvay Company (December 2011), Product Safety Summary of Trifluoroacetyl chloride (TFAC) (PDF), retrieved October 16, 2013
  14. ↑ Kevin James Coe (2008), Metabolism and Cytotoxicity of the Nitroaromatic Drug Flutamide and Its Cyano Analog in Hepatocyte Cell Lines, ISBN   9781109000955 , retrieved October 22, 2013
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.