Pentafluorobenzoyl chloride

Analyses of derivatives of NPEOs have been carried out with a large number of derivatisation reagents. Among them, polyfluorinated reagents, such as pentafluorobenzoyl chloride and heptafluorobutyric... 

FLUORINECOMPOUNDS,ORGANIC - FLUORINATED AROMATIC COMPOUNDS] (Volll) Pentafluorobenzoyl chloride [2251-50-8]... 

Koster et al. [140] conducted on-fiber derivatization for SPME to increase the detectability and extractability of drugs in biological samples. Amphetamine was used as a model compound. The extraction was performed by direct immersion of a 100-pm polydimethylsiloxane-coated fiber into buffered human urine. On-fiber derivatization was performed with pentafluorobenzoyl chloride either after or simultaneously with extraction. 

Chlorophenols derivitivised with acetic anhydride or pentafluorobenzoyl chloride... 

Carbonyl chloride or acetic anhydride Picolinoyl chloride [64] 4-Nitrobenzoyl chloride [60] Pentafluorobenzoyl chloride [65] Acetic anhydride [66] Both phenolic OH and alcoholic OH LC-ESP/MS/ MS LC-APCI/ MS/MS GC-EP/MS LC-APCP/ MS2... 

In these investigations, the authors subjected PAF to direct derivatization with pentafluorobenzoyl chloride (PFB) or heptafluorobutyric anhydride (HFB). Using a 16 0 PAF, the resulting reaction sequence is presented in Figure 6-3. The reaction mixture is evaporated under a stream of nitrogen, and the residue is partitioned between hexane and water. The derivatives noted above are found in the hexane layer, and the polar head group is located in water-soluble fraction. 

Weintraub, S. T., Lear, C. S., and Pinckard, R. N. (1990) Analysis of platelet-activating factor by GC-MS after direct derivatization with pentafluorobenzoyl chloride and heptafluorobutyric anhydride, J. Lipid Res. 31, 719-725. 

The anhydrides and chloroanhydrides of chlorinated acetic acids and pentafluorobenzoyl chloride are used for the synthesis of chlorinated amides for GC analysis with selective detectors. Diethylpyrocarbon-ate converts primary and secondary amines (including NH3) to N-substituted carbamates ... 

Parameters such as solvent, basic medium and reaction time, affecting the derivatization of alcohols and phenols with benzoyl chloride, were investigated. End analysis was by GC with UVD . a sensitive method proposed for trace determination of phenols in water consists of preconcentration by SPE with a commercial styrene-divinylbenzene copolymer, acylation with pentafluorobenzoyl chloride in the presence of tetrabutylammonium bromide and end analysis by GC with either ECD or ITD-MS. LOD was 3 to 20 ngL for ECD and 10 to 60 ngL for ITD-MS, with 500 mL samples . Acylation with the fluorinated glutaric acid derivative 43 was proposed for determination of urinary phenols, as indicative of exposure to benzene and other aromatic hydrocarbons. End analysis by GC-MS shows strong molecular ions of the derivatives by electron ionization. The proto-nated ions are the base peaks obtained by chemical ionization. LOD was 0.5 mgL and the linearity range 0-100 mg L for phenol . 

Derivatize with pentafluorobenzoyl chloride extract with methylene chloride... 

The reaction of 2-mercaptobenzimidazole with pentafluorobenzoyl chloride forms 1,2,3,4-tetrafluoro-12//-benzimidazo[2,1 -b, 3]benzo-thiazin-1,2-one (yield 50%), whose structure was confirmed by X-ray data (94JOC7688) (Scheme 165). 

The formation of a heterocyclic system by intramolecular elimination of the ort/m-fluorine atom of an aromatic ring was demonstrated by the reaction of pentafluorobenzoyl chloride with 2-imidazolidinethione or 2-mercaptoimidazole, forming 6,7,8,9-tetrafluoro-2,3-dihydro-5//-imidazo-[2,1 -6][l,3]-benzothiazin-5-one (yield 54%) and 6,7,8,9-tetrafluoro-5//-imidazo[2,l-6][l, 3]benzothiazin-5-one (yield 48%) (94JOC7688) (Scheme 166). 

If the starting nucleophilic agent has an S = C-N triad, the cyclization involves the nucleophilic centers on sulfur and nitrogen atoms. Thus, the interaction between pentafluorobenzoyl chloride and pyrimidine-2-thione 181 forms tetrafluorobenzo-thiazinopyrimidinone 182 (94JOC7688) (Scheme 167). 

By utilizing fluorocarbon fluids containing pentafluorobenzoyl chloride, a liquid microcarrier system has been developed capable of use with a variety of cell types including normal human fibroblast. In this configuration, cells on the surface of a coarse oil dispersion ( 150 /im diameter) exhibit exponential growth (Figure 7). In addition, a microcarrier based on silicone oil has been formed and used to culture mouse fibroblasts (12-13). 

Method 1403 (see Section 21.2). EGBE or its metabolites in the blood or urine can be analyzed by HPLC techniques. Blood or urine samples may also be analyzed by derivatiz-ing EGBE with pentafluorobenzoyl chloride and then analyzing by GC with an electron-capture detector (Johansson et al. 1986). 

Notes Measured by SEC, 70/20/10 (v/v/v) mixture of dichloromethane/chloroform/1,1,1,3,3,3-hexafluoro2-propanol (HFIP) 70/20/10 was used as the eluent, compared to polystyrene [17]. Measured by elemental analysis after hydroxyl end-group functionalization with pentafluorobenzoyl chloride [17]. Measured by SEC, HFIPaseluent, compared to polymethylmethacrylate [49. Measured by SEC, HFIP as eluent, compared to polymethylmethacrylate [471. Ref. 170). Refs. 14, 34, 70. ... 

Recently, m our laboratories, an improved method for quantitative analysis of amino acids has been developed (Yeung, Baker, and Courts, manuscript in preparation). The carboxylic acid moiety IS derivahzed quantitatively by adding one drop of concentrated HCl to an isobutanol solution of the amino acids, rather than bubbling HCl gas in the conventional manner, prior to heating. Benzoyl chloride is known to be more reactive chemically than acid anhydrides, and pentafluorobenzoyl derivatives are highly sensitive to electron-capture detection (Moffat et al., 1972, Matin and Rowland, 1972, McCallum and Armstrong, 1973 Midha et al., 1979 Cristofoli et al, 1982, Nazarali et al., 1983). Pentafluorobenzoyl chloride (PFBC), therefore, was chosen to derivatize the other reactive groups of the amino acid isobutyl esters. Pentafluorobenzoylation (Fig. 7) was conducted at room temperature in aqueous conditions. 

Figure 1. The effect of polytetrafluoroethylene on perfluoroacyl derivatization. The profile in curve A was obtained from derivatization of / -phenylethylamine (PE) with pentafluorobenzoyl chloride (PFBzO-Q) in an zill-glass system, that in curve B from the same reaction in a reaction vial sealed with a polytetrafluoroethylene-lined cap. Peak 1 PE derivative peak 2 derivative of the internal standard, tolylethylaminc (Ref. 13). Note the major peak of pentafluorobenzoic acid, the other by-products, and the reduced yield of derivatives in profile B.

Pentafluorobenzoyl chloride (10 % solution in nanograde toluene) (e.g. Fluka, Art. No. 76733)... 

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