《Scission of diaryl ethers and related compounds by means of piperidine. II. The nitration of 2,4,4′-trichlorodiphenyl ether and of 2,4-dichlorophenyl p-toluenesulfonate and benzoate》 was published in Journal of the Chemical Society in 1929. These research results belong to Groves, Leslie G.; Turner, Eustace E.; Sharp, Gladys Irene. Recommanded Product: 38902-87-3 The article mentions the following:
cf. C. A. 21, 2673. 2,4-Cl2C6H2OH is obtained in 80% yield from p-ClC6H4OH; the p-toluenesulfonate, m. 125°; nitration gives 2,4-dichloro-5-nitrophenyl o-nitro-p-toluenesulfonate (I), m. 103°; reduction with Fe and a little AcOH gives the diamino derivative, m. 159-61°; the diazo solution, with CuCl-HCl, gives a red gum which, refluxed 3 hrs. with piperidine, gives 2,4,5-Cl3C6H2OH, m. 66-7°. 1-p-Toluenesulfonylpiperidine, m. 103°; o-NO2 derivative (II), pale greenish yellow, m. 112°. Heating I with 1/3 of its weight of piperidine for 1.5 hr. at 100° gives II and 2,4-dichloro-5-nitrophenol (III), m. 105-6°. N-2,4-Dichlorophenylphthalimide, m. 155°; HNO3 in cocnd. H2SO4 gives the 5-NO2 derivative, pale yellow, m. 217-9°, saponified by 90% H2SO4 to 2,4,5-Cl2(O2N)C6H2NH2. 2,4-(O2N)2C6H3Cl and 2,4-Cl2C6H3OH in KOH give 2,4-dichloro-2′,4′-dinitrodiphenyl ether, pale greenish yellow, m. 118-9°; nitration gives the 5,2′,4′-tri-NO2 derivative, m. 128°; scission with piperidine gives III, while PhNH2 gives III and 2,4-(O2N)2C6H3NHPh. 4,4′-Dichloro-2-aminodiphenyl ether, m. 67°, results in 90% yield by reduction of the NO2 derivative with Fe and a little AcOH; through the diazo reaction there results 2,4,4′-trichlorodiphenyl ether, b11 183°, m. 54-5°; 2′-NO2 derivative, m. 86-7°, decomposed by piperidine into 2,4-Cl2C6H3OH and 4-chloro-2-nitrophenylpiperidine. The 5,2′-di-NO2 derivative, pale yellow, m. 103-4°, is decomposed by piperidine to give III. 2,4,4′-Trichloro-5,2°-diamino-diphenyl ether, m. 93-4°. 2,4,4′-Trichloro-5,2,5′-trinitrodiphenyl ether, yellowish green, m. 155-7°; piperidine gives III and 4-chloro-2,5-dinitrophenylpiperidine, red, m. 70-1°. 4-Chloro-2,6-dinitrophenylpiperidine, golden, m. 165-6°, results from 4,2,6-Cl(O2N)2-C6H2OMe. 2,4-Dichloro-5-nitrophenyl m-nitrobenzoate, m. 154°; 2,4-dichlorophenyl m-nitrobenzoate, m. 115-6°, gives the same product on nitration. 2,4-Dichloro-6-nitrophenyl m-nitrobenzoate, m. 149-50°, was prepared for purposes of comparison. Chlorination of m-O2NC6H4OH gives 2,4-dichloro-3-nitrophenol, pale yellowish green, m. 85-7°; p-totuenesulfonyl derivative, m. 122°, reduced by Fe and a little AcOH to the 3-NH2 derivative, m. 113-4°; the diazo solution, treated with CuCl-HCl and the crude product heated with piperidine, gives 2,3,4-trichlorophenol, m. 80-1°, identical with that obtained by chlorinating 3,4-Cl2C6H3OH. III does not react with SOCl2 and gave no definite product with PCl3. 4,5,1,2,-Cl2C6H2(NO2)2 and PhOK give 4,5-dichloro-2-nitrodiphenyl ether, yellow, m. 69-70°. 4,5,4′-Trichloro-2-nitrodiphenyl ether, pale yellow, m. 131-2°, decomposed by piperidine, giving 4-chloro-2-nitrophenylpiperidine. 4,5,2′,4′-Tetra-chloro-2-nitrodiphenyl ether, pale yellow, m. 125-6°; the 2-NH2 derivative m. 97-8°. The experimental part of the paper was very detailed, including the reaction process of 2,4-Dichloro-3-nitrophenol(cas: 38902-87-3Recommanded Product: 38902-87-3)
2,4-Dichloro-3-nitrophenol(cas: 38902-87-3) belongs to organochlorine compounds. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties.Recommanded Product: 38902-87-3 Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics