Trifluoroacetyl chloride
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| Names | |||
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Preferred IUPAC name
Trifluoroacetyl chloride
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| Other names
2,2,2-Trifluoroacetyl chloride
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3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.005.961 | ||
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| Properties | |||
| C2ClF3O | |||
| Molar mass | 132.469 | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
Trifluoroacetyl chloride (also known as TFAC) is a gaseous chemical compound with the chemical formula C2ClF3O. It is usually shipped as a liquid under high pressure, however. The compound is a toxic gas.
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. The compound has a melting point of −146 °C (−231 °F) and a boiling point of −27 °C (−17 °F). The compound easily reacts with water and moist air to produce the toxic gas hydrogen chloride and trifluoroacetic acid.
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.
Trifluoroacetyl chloride's heat of vaporization is 20 kilojoules per mole at 65 btus per pound.
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.
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