Fluoroacetyl chloride

C, which decomposes when heated above the melting point. Its solubility at 25°C in g/100 g solvent is water. 111 methanol, 5 ethanol, 1.4 acetone, 0.04 and carbon tetrachloride, 0.004. Because its carbon—fluorine bond is unreactive under most conditions, this salt can be converted by standard procedures to typical carboxylic acid derivatives such as fluoroacetyl esters (11,12), fluoroacetyl chloride [359-06-8] (13), fluoroacetamide (14), or fluoroacetonitrile [503-20-8] (14). 

N-(2-Amino-5-Nltrobenzyl)-o-Toluidine Fluoroacetyl Chloride Acetic Anhydride Hydrogen... 

Ferroglycine sulfate Ferrous fumarate Fluoranthene Flora ntyrone Fluoroacetyl chloride Afloqualone p-Fluorobenzaldehyde Sulindac Fluorobenzene Flubendazole o-Fluorobenzoyl chloride Flunitrazepam... 

Fluoroacetyl chloride, CH2FCOCl, was prepared by the action of phosphorus pentachloride on the free fluoroacetic acid (p. 121).1 It is extremely useful as fluoroacetylating agent in synthetic work. Because of its importance we have recently reinvestigated other methods of preparation.2 These may be summarized as follows (1) direct from fluoroacetamide (p. 125) by the action of phosphorus oxychloride and water (2) the action of phosphorus oxychloride on either sodium fluoroacetate (p. 121) or on barium fluoroacetate (p. 121). Good yields are obtained in both (1) and (2), and in each case the starting materials are more easily available than fluoroacetic acid itself. 

It is interesting to compare the toxicity of fluoroacetyl chloride with the isomeric chloroacetyl fluoride. The former possessed a toxicity comparable to that of methyl fluoroacetate, whereas the latter was relatively non-toxic. This is readily understandable in that fluoroacetyl chloride gives the toxic fluoroacetic acid, whereas chloroacetyl fluoride hydrolyses to chloroacetic acid and the relatively non-toxic (at the concentrations employed) hydrogen fluoride. Fluoroacetyl fluoride also possessed a toxicity comparable with that of fluoroacetyl chloride or of methyl fluoroacetate, again showing that the COF group contributed practically nothing. Acetyl fluoride was also non-toxic. 

Fluoroacetic anhydride, which was readily prepared by the action of fluoroacetyl chloride on sodium fluoroacetate, is a mobile liquid of b.p. 89°/12 mm. It is a useful fluoroacetylating substance. It was rather more toxic by inhalation than M.F.A. (weight for weight). 

In view of the well-known pharmacological action of aspirin, it was thought that the fluorine analogue, O (fluoroacetyl) salicylic acid, might be of considerable interest. The compound was readily made by acylation of salicylic acid by fluoroacetyl chloride in the presence of pyridine. The l.d. 50 for subcutaneous injection into mice was approximately 15 mg./kg. After injection the mice went into a drugged sleep, and died overnight. 

N-2-Chloroethylfluoroacetamide was also prepared by the direct action of 2 mol. of fluoroacetyl chloride on ethanolamine, although we carried out this reaction with the intention of preparing 2-(fluoroacetamide)ethyl fluoroacetate,... 

In view of the fact that fluoroethanol is as toxic as methyl fluoroacetate (or as fluoroacetic acid), it seemed worth while preparing a compound in which the active parts of these molecules were combined, in the hope of obtaining a compound of increased potency. Such a compound is 2-fluoroethyl fluoroacetate, first prepared and described by us in 1943.1 This ester was readily prepared by the action of fluoroacetyl chloride on fluoroethanol. It is a stable, mobile liquid possessing an extremely faint odour. 

Class B Fluoroacetic acid and salts, e.g. sodium fluoroacetate, triethyl-lead fluoroacetate all simple esters of fluoroacetic acid fluoroacetamide and substituted amides fluoroacetamidine hydrochloride fluoroacetyl chloride and fluoride fluoro-ethanol and its simple esters fluoroacetaldehyde. 

Condensation with imines to afford jS-lactams. These latter ones can also be obtained by cycloaddition of the same imines with the keten stemming from fluoroacetyl chloride. ... 

Trifluorothreonine is one of the rare fluorinated compounds found in nature (cf. Chapter 4). The best method for the synthesis of fluorothreonines is the acylation of an equivalent of glycinate anion by a fluoroacetic derivative. The four stereoisomers of monofluorothreonine have been prepared. A completely stereoselective chiral approach involves the alkylation of the Seebach imidazolidinone by fluoroacetyl chloride (Figure 5.16). ... 

EPOXIDES Alumina. r-Butyldimethyl-iodosilane. n-Butyllithium-Magnesium bromide. Cyclohexylisopropylamino-magnesium bromide. Dialkylaluminum amides. lodotrimethylsilane. Lithium l-a,a -dimethyldibenzylamide. Nafion-H. Organoaluminum compounds. Pyri-dinium chloride. Raney nickel. Tti-fluoroacetyl chloride, lrimethylsilyl-acctonitrile. Tris(phenylscleno)borane. Zinc iodide. 

The method is applied to the greatest extent in making jluoro acyl halides such as fluoroacetyl chloride from sodium fluoroacetate and phosphorus pentachloride. The products are distilled from a mixture of the dry reagents, usually without a solvent. Phosphorus trichloride and phosphorus oxychloride have also been used for the preparation of compounds of this type. 

Fluoroacetamlde Fluoroaceticacid Fluoroacetyl chloride FluoroaceF/lene... 

Fluoroacetamlde Fluoroacetic acid Fluoroacetyl chloride Fluoroacetylene... 

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