Anthracene-9-carbonyl chloride

Phenyl isothiocyanate (PITC) and 3.1.5 Anthracene-9-carbonyl chloride 169... 

Recently, Bayliss et al. [132] described the synthesis of anthracene-9-carbonyl chloride and its aplications as a label for fluorescence and UV absorbance detection of hydroxy compounds. The preparation and properties of esters of short-chain alcohols, diols, trichothecene mycotoxins and sterols were investigated. Anthracene-9-carbonyl chloride was prepared from commercial anthracene-9-carboxylic acid. Derivatization was carried out in acetonitrile free from water or active hydrogen compounds. The reaction rate was dejjendent on the structure of the alcohol. The derivatization of diethylene glycol was complete at ambient temp>erature within 10 min (0.25 M reagent) or 30 min (0.1 M reagent) without a catalyst, but required 1 h for diolesteroL testosterone and the trichothecene T-2 toxin. For sterically hindered alcohols such as t-butanol and 17a-methyl-testosterone, more than 10 h, or refluxing for 1 h, was needed to complete the reaction. The derivatives had absorption maxima at 250 run. Both normal and reversed phase HPLC were applied to the separation of the derivatives. 

Friedel-Oafts diacylation of dibenzothiophene with 7-oxo-lH-benzo[d,e]anthracene-3-carbonyl chloride, followed by ring closure in molten sodium chloride-aluminum chloride, is reported to yield 131 which is claimed to be useful as an orange dyestuff. No evidence for the structure of 131 was presented although analogous succinoylation studies (Section VI,G,2) would indicate that the structure is correct. 

Anthracene Arsenic trifluoride Benzyl chloride Benzyl cyanide Boron trifluoride Bromine trifluoride Butyl lithium Butyl mercaptan Calcium arsenide Carbon bisulfide Carbon monoxide Carbonyl fluoride Carbonyl sulfide Chlorine monofluoride Chlorine trifluoride Chloroacetic anhydride Chloroacetyl chloride Chloroform Chrysarobin Coal tar Cyanogen... 

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