Pentachlorophenyl chloride

Synonyms AI3-01719 AIDS-17533 Amatin Anticarie BRN 1912585 Bunt-cure Bunt-no-more Caswell No. 477 CCRIS 325 Co-op hexa EINECS 204-273-9 ENT 1719 EPA pesticide chemical code 061001 Granox Granox NM HCB HCBz Hexa C.B. Julen s carbon chloride Julian s carbon chloride Julin s carbon chloride Julin s chloride No bunt No bunt 40 No bunt 80 No bunt liquid NSC 9243 Pentachlorophenyl chloride Perchlorobenzene Phenyl perchloryl RCRA waste number U127 Sanocid Sanocide Smut-go Snieciotox UN 2729 Voronit C. 

Synonyms Hexachlorobenzol perchloroben-zene HCB pentachlorophenyl chloride... 

PENTACHLOROPHENOL, DP-2 see PAX250 PENTACHLOROPHENOL, SODIUM SALT see SJAOOO PENTACHLOROPHENOL, TECHNICAL see PAX250 PENTACHLOROPHENOXY SODIUM see SJAOOO PENTACHLOROPHENYL CHLORIDE see HCC500 PENTACHLORURE d ANTIMOINE (FRENCH) see AQDOOO... 

PENTACHLOROPHENYL CHLORIDE (118-74-1) Combustible liquid (flash point 467°F/242°C). Violent reaction with strong oxidizers, dimethylformamide, liquid oxygen. Incompatible with aluminum, potassium, sodium. 

Synonyms Benzene, hexachloro- HCB Hexa C.B. Pentachlorophenyl chloride Perchlorobenzene Phenyl perchloryl... 

Pentachlorophenol. See Pentachlorophenol Pentachlorophenol, sodium salt Pentachlorophenoxy sodium. See Sodium pentachlorophenate Pentachlorophenyl chloride. See Hexachlorobenzene Pentachlorothiophenol CAS 133-49-3... 

We were able to prepare pentachlorophenylmagnesium chloride 5>, pentachlorophenyl-lithium 7 9>, and tetrachloroanthranilic acid 19>, relatively easily. However, we found that pentabromophenyl-lithium could not be formed in an acceptable yield from hexabromobenzene and that tetrabromoanthranilic acid was not readily available by the published methods. The preparation of tetrabromoanthranilic acid, in high yield (>85%), has now been achieved, and we find that all of the tetra-halogenbenzynes react with benzene with the exclusive formation of the 1,4-cyclo-adduct in good yield. The adduct of tetrabromobenzyne with benzene has been prepared very recently in 3% yield from pentabromophenyl-lithium 58>. 

Octachlorodibenzothiophene (88) has been formed by irradiation of a solution of pentachlorobenzenesulfenyl chloride in CCI4 in a low-pressure, cold cathode mercury arc (62%). A similar photolysis of bis-(pentachlorophenyl) sulfide, prepared by the action of sulfur monochloride and sulfuryl chloride on benzene in the presence of aluminum chloride, also yielded 88 (42%). Both routes are shown in Scheme 4. 

Methylene chloride-soluble residues. Methylene chloride-or chloroform-soluble C-labeled products were major residues in all of the plant tissues examined except peanut cell ciiltures (Figure 3). Chloroform-soluble C accounted for 59.2 of the radioactivity isolated from peanut roots 48 hr after treatment with [ C]PCNB. The radioactivity was in the form of PCNB (28.7 ), pentachloroaniline (22.5 ), pentachlorothiophenol (2.6 ) pentachlorothloanlsole (3.1 ) pentachlorothloanlsole sulfoxide (0.5 ) S-(pentachlorophenyl)-2-thioaoetic acid [(S-(PCP)ThioAcetate] (0.5 ) and S-(pentachlorophenyl)-3-thio-2-hydroxypropionic acid [S-(PCP)ThioLactate] (0.2 ) and S-(PCP)Cys (trace) (J), The structures of these compounds are shown in Figure 13. Based on TLC, the last three compounds in this list were classified as polar chloroform- or methylene chloride-soluble residues and the remaining compounds were classified as nonpolar residues. 

A solution of pentachlorophenylmagnesium chloride" is prepared from hexachlorobenzene (66 g, 0.23 mol) and magnesium (8.44 g, 0.35 mol) in a mixture of THF (150 ml) and benzene (150 ml) (HAZARD toluene would be preferable). The solution is heated to reflux, and ethyl formate (40 ml, excess) is added by syringe at such a rate that the exothermic reaction maintains refluxing. The mixture is stirred as it is allowed to cool to room temperature during 1 h. Methanol (20 ml) is added, and the solvents are evaporated. The resulting dark-brown residue is washed with hydrochloric acid, methanol and ethyl acetate, and then recrystallized from 4 1 toluene-pyridine, to give bis(pentachlorophenyl)methanol (35 g, 29%). 

Reaction of chloromethyl pentachlorophenyl sulfone with aromatic aldehydes provided Z vinyl chlorides exclusively in high yields (Judka and Makosza, 2006, personal communication). 

Peptide synthesis, N-protection Acetic-formic anhydride. Adamantyl chloroformate. Benzylthiocarbonyl chloride. /-Butoxycarbonyl-N-hydroxysuccinimide ester. /-Butyl azido-formate. /-Butylcarbonic diethylphosphoric anhydride. /-Butyl fluoroformate. /-Butyl oxycarbonyl fluoride. /-Butyl pentachlorophenyl carbonate. /-Butyl 2,4,5-trichlorophenyl carbonate. Carbobenzoxy chloride. 3,5-Dimethoxybenzyl p-nitrophenyl carbonate. [2-(Diphenyl)isopropyljphenyl carbonate. /-Pentyl chloroformate. 

Perhalogenated aromatic compounds also yield Grignard reagents on reaction with magnesium e.g.9 (pentachlorophenyl)magnesium chloride is formed from hexachlorobenzene in tetrahydrofuran,119 and (pentafluorophenyl)-magnesium bromide from bromopentafluorobenzene.120... 

Aminopyridine is reported to react vigorously with chlorosulfonyl isocyanate at 0°C producing an urea intermediate (12) which in the presence of diisopropylethylamine was shown to yield pyrido[l,2-i][l,2,4,6]thiatriazine-5(6/0 OIte-l l-dioxide (2) (Scheme 3) <79H(6)815>. Its V-benzyl derivative (3) was selectively prepared by the reaction of 2-benzylaminopyridine (13) with either chlorosulfonyl isocyanate via intermediate (15) or pentachlorophenyl chlorosulfonyl carbamate (PCPCSC) in the presence of diisopropylethylamine via intermediate (14) (Scheme 4) <86H(8)2255>. The reaction of 2-alkyl-2-chlorosulfonyl carbamoyl chlorides with 2-aminopyridine resulted in 2-alkylpyrido [l,2-i ][ 1,2,4,6]thiatriazine-3(2/0-one-1,1-dioxides (5) (Equation (2)) <77CR(S)238>. 

Bis(pentachlorophenyl)thallium chloride has been used as an arylating reagent for various transition-metal complexes. ... 

Only a few examples of 2,5-morpholinediones prepared via route B have been reported. Shemyakin et al. [12] prepared cyclic depsipeptides by cyclization of the acid chlorides of aminoacyl hydroxy acids, whereas Goodman and coworkers [13] found 2,5-morpholinediones to be the main products in the polymerization of trifluoroacetate salts of the aminoacyl hydroxy acids pentachlorophenyl esters. 

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