Clark, N. G.; Cranham, J. E.; Greenwood, D.; Marshall, J. R.; Stevenson, H. A. published an article in 1957, the title of the article was Toxicity of organic sulfides to the eggs and larvae of the glasshouse red spider mite. III. Benzyl phenyl sulfides substituted only by halogens.Synthetic Route of 53136-21-3 And the article contains the following content:
Nuclear halogenation had a strong effect on the biol. activity of benzyl Ph sulfide, which was virtually inactive. In monosubstituted compounds, substitution in the para position of the Ph moiety gave products much less active than the corresponding compounds substituted in the para position of the benzyl moiety. With substituted Ph compounds there was a general rise in activity from F through Cl and Br to I. With few exceptions, all compounds substituted by halogen in the para position of both nuclei or in the benzyl moiety only were of high activity. Position of substitution played a role in activity, ortho-substituted benzyl derivatives being relatively less active. Substitution by more than 1 halogen atom in either nucleus resulted in compounds of lower activity than the corresponding compounds substituted only in the para positions. The following newly synthesized compounds were among those evaluated: XC6H4CH2SC6H4Y (X, Y, and m.p. (or b.p.) given): H, p-F, 32.5-33°; H, I, 52-3°; H, 2,4,-5-Cl3, 118-19°; H, 2,5-Cl2, 65°; H, p-Br, 64-5°; H, p-I, 77°; p-F, H, 62-2.5°; p-F, p-F, 44.5-5.5°; p-F, I, 49-50°; p-F, p-Br, 56.5-7.5°; p-F, p-I, 75°; ο-Cl, p-F, b1.5, 141-3°; ο-Cl, I, b2.0 170°, m. 32°; m-Cl, p-F, b2.0 158-60°; m-Cl, I, b2.0 172-5°; I, H, 78°; I, p-F, 34.5-5.5°; I, I, 72°; I, 2,5-Cl2, 113-14°; I, 2,4,5-Cl3, 76-7°; I, p-Br, 87-8°; I, p-I, 102°; 2,4-Cl2, H, b1.5 163-5°; 2,4-Cl2, p-F, 167°; 2,4-Cl2, I, 58-9°; 2,6-Cl2, H, 39-40°; 2,6-Cl2, p-F, 51°; 2,6-Cl2, I, 69-70°; p-Br, H, 78°; p-Br, p-F, 44-5°; p-Br, I, 83-4°; p-Br, p-Br, 101°; p-Br, p-I, 116°; p-I, H, 88°; p-I, p-F, 56°; p-I, I, 101°; p-I, p-Br, 118°; and p-I, p-I, 131°. XC6H4CH2SOnC6H4Y (X, Y, n, and m.p. given): H, p-F, 1, 138-40°; H, p-F, 2, 153.5-4.5°; H, I, 1, 134°; H, I, 2, 144-5°; H, p-Br, 1, 141-2°; H, p-Br, 2, 158-9°; H. p-I, 1, 128°; H, p-I, 2, 182°; p-F, p-F, 1, 160-1°; p-F, p-F, 2, 186-7°; p-F, I, 2, 156-7°; p-F, p-Br, 2, 171.5-72°; p-F, p-I, 1, 171°; p-F, p-I, 2, 201°; o-Cl, p-F, 2, 107-8°; o-Cl, I, 1, 73-4°; o-Cl, I, 2, 120-1°; m-Cl, p-F, 1, 82.5-3.5°; m-Cl, p-F, 2, 135-6°; m-Cl, I, 1, 94-6°; m-Cl, p-Cl, 2, 125° and 130°; I, H, 1, 173°; I, H, 2, 190°; I, p-F, 1, 125-6°; I, p-F, 2, 144-5°; I, I, 1, 124°; I, I, 2, 150°; I, p-Br, 1, 132-3°; I, p-Br, 2, 169-70°; I, p-I, 1, 159°; I, p-I, 2, 194°; p-Br, H, 1, 179°; p-Br, H, 2, 192-3°; p-Br, p-F, 1, 141°; p-Br, p-F, 2, 160-1°; p-Br, I, 1, 135-6°; p-Br, I, 2, 158-9°; p-Br, p-Br, 1, 145-6°; p-Br, p-Br, 2, 179-80°; p-Br, p-I, 1, 180°; p-Br, p-I, 2, 213°; p-I, H, 1, 191°; p-I, H, 2, 209°; p-I, p-F, 1, 171°; p-I, p-F, 2, 196°; p-I, I, 1, 153°; p-I, I, 2, 187°; p-I, p-Br, 1, 171°; p-I, p-Br, 2, 202°; p-I, p-I, 1, 197°; and p-I, p-I, 2, 239°. The experimental process involved the reaction of Benzyl(4-bromophenyl)sulfane(cas: 53136-21-3).Synthetic Route of 53136-21-3
Benzyl(4-bromophenyl)sulfane(cas:53136-21-3) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Synthetic Route of 53136-21-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem