 | |||
| |||
| 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 | ||
| EC Number |
| ||
| UNII | |||
| UN number | 3057 | ||
| |||
| |||
| 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: | |||
   | |||
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Trifluoroacetyl chloride (also known asTFAC[1]) is a toxic gaseouschemical compound with thechemical formulaC2ClF3O.[2][3] TFAC is the perfluorinated version ofacetyl chloride. The compound is a gas, but it is usuallyshipped as a liquid under high pressure.[3]
Trifluoroacetyl chloride has avapor density that is 4.6 times that ofair, or about 1.384 grams per milliliter at 20 °C (68 °F) as a liquid under pressure.[1][2] The compound has amelting point of −146 °C (−231 °F) and aboiling point of −27 °C (−17 °F).[2] The compound easily reacts withwater and moist air to produce the toxic gashydrogen chloride andtrifluoroacetic acid.[3][4]
Trifluoroacetyl chloride isincompatible with a number of other varieties of chemicals, such asamines,alcohols,alkalis, and strongoxidizers. It reacts strongly with amines and alkalis. It also reacts violently withdiisopropyl ether, or anyether if metalsalts are present, sometimes causing an explosion.[3]
Trifluoroacetyl chloride'sheat of vaporization is 20kilojoules permole at 65btus per pound.[1]
Numerous atoms and compounds can replace the chlorine atom in trifluoroacetyl chloride. These includeiodine,fluorine,cyanide,thiocyanate, andisocyanate. The compound also reacts easily with metalalkyls. This reaction has the form of CF3COCl + MR → CF3COR + MCl, where M can belithium,copper,magnesium,mercury,silver, orcadmium. When trifluoroacetyl chloride also reacts withketene andesterification yields occur, the resulting reaction formstrifluoroacetoacetateesters.[1]
Trifluoroacetyl chloride also reacts withsoil,cellulose-based absorbents, andclay-based absorbents.[5] When the compound reacts with water in contact with metal,hydrogen gas, which is explosive, is produced.[6] The compound forms aclustering reaction with amethyl group (CH3).[7]
Trifluoroacetyl chloride can be produced bycatalyticchlorination of chlorine andtrifluoroacetaldehyde.[8] The compound can also be produced ifhalothane is oxidized usingCYP2E1.[9] This is also done withCYP2A6 instead of CPY2E1, but less readily.[10]
Trifluoroacetyl chloride's applications include uses inmedicine,pesticides, the fine chemical industry, and the organicintermediate industry.[3] However, the compound itself is not sold toconsumers or as acommodity.[4] Someacetoacetic esters produced by trifluoroacetyl chloride are in turn used to perform chemical reactions that result in the formation of compounds withagricultural andpharmaceutical applications.[1]
One of trifluoroacetyl chloride's uses is in addingtrifluoromethyl to complex molecules duringchemical reactions.[1]
In the late 1970s, trifluoroacetyl chloride was explored for use as areagent fornuclear magnetic resonance. It was intended to be used onamines,alcohols,thiols, andphenols.[11]
Trifluoroacetyl chloride is typically stored as a liquid under high pressure.[4]
Liquid trifluoroacetyl chloride can causefrostbite if it comes in contact with unprotected skin. If inhaled, the compound in its gaseous state will irritate theeyes,skin, andmucous membranes. Trifluoroacetylchloride is atoxic 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 therespiratory tract.[4] The compound is also alacrimator. It can causedyspnea if inhaled bymice,rats, orguinea 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 notbioaccumulate significantly. However, it is harmful toaquatic organisms.[13]
Trifluoroacetyl chloride is metabolized byCytochrome P450enzymes. Theimmune systems of organisms typically react to this.[14]
