On November 17, 1954, there was a patent about dyes.Computed Properties of 452-75-5 The title of the patent was Anthraquinone vat dyes. And the patent contained the following:
A series of anthraquinone vat dyes of the general formula I, where R is p-ClC6H4CONH, or 2,4-F(Cl)C6H3CONH, or 2,5-F(Cl)C6H3CONH and A represents a dicarboxylic acid residue, was prepared Thus, 1-amino-5-(4-chloro-2-fluorobenzamido)anthraquinone (II) 5.9 and p-ClC6H4COCl 4 parts heated 0.5 hr. with stirring in C6H3Cl3 150 at 200-5°, the mixture cooled and filtered, and the residue washed with EtOH and dried gave a dye which could be purified further with hypochlorite solution, red in concentrated H2SO4, dyed cotton from a Bordeaux-colored Na2S2O4 vat fast pure-yellow tints. The 5-Cl isomer of II gave similarly a dye yielding somewhat more reddish yellow dyeings. II, m. 279°, was prepared by the acylation of 1,5-diaminoanthraquinone with 2,4-F(Cl)C6H3COCl (III) or from 1-chloro-5-(4-chloro-2-fluorobenzamido)anthraquinone by replacing the 1-Cl atom by a p-MeC6H4SO2NH residue followed by cleavage. The 5-Cl isomer of II, m. 269°, was prepared in the same manner. 2,4-F(Cl)C6H3Me, b743 158°, obtained from 2,4-NH2(Cl)C6H3NH2 through the diazonium fluoborate, gave by KMnO4 oxidation 2,4-F(Cl)C6H3CO2H (IV), m. 205°. IV treated with SOCl2 yielded III, b14 105-6°. 2,5-H2N(Cl)C6H3Me was converted through the diazonium fluoborate to 2,5-F(Cl)C6H3Me, b741 156°, and further to 2,5-F(Cl)C6H3CO2H, m. 149-50°, which yielded 2,5-F(Cl)C6H3COCl, b15 103-4°. II 7.9, (COCl)2 1.27, and C6H3Cl3 150 parts heated with stirring during 2 hrs. to 150°, the mixture heated further to 190°, kept 1 hr. at 190-200°, cooled to 100°, and filtered, and the residue washed with EtOH and dried (it may be purified by boiling the neutral aqueous suspension with hypochlorite) gave I, where A = O:CC:O and R = 2,4-F(Cl)C6H3CONH, Bordeaux in concentrated H2SO4, which dyed cotton fast greenish yellow tints from a Bordeaux vat. II 4,p-C6H4(COCl)2 1, and C6H3Cl3 150 parts refluxed 2 hrs. with stirring gave I, where A = p-O:CC6H4C:O and R = 2,4-F(Cl)C6H3CONH, which dyed cotton fast pure yellow tints. Thianthrene dicarboxylic acid 1.12, SOCl2 6, pyridine 0.05, and C6H3Cl3 90 stirred 0.5 hr. at 80° and then 0.5 hr. at 120°, the excess SOCl2 and some of the solvent distilled off. the residual solution cooled to 100° and treated with II 3 parts, and the mixture heated 2 hrs. at 200-10°, cooled to 120°, and filtered gave I, where R = 2,4-F(Cl)C6H3CONH and A = thianthrenedicarbonyl, red in concentrated H2SO4, dyed cotton fast yellow tints. The experimental process involved the reaction of 4-Chloro-2-fluorotoluene(cas: 452-75-5).Computed Properties of 452-75-5
4-Chloro-2-fluorotoluene(cas:452-75-5) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Computed Properties of 452-75-5
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics