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Timestamp: 2019-04-23 19:50:34+00:00

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Physical Data: bp 55-56 °C; d 1.010 g cm-3; nD20 1.4935.
Form Supplied in: colorless liquid; commercially available, stabilized with 0.5% BuSH.
Handling, Storage, and Precautions: highly toxic,6 flammable liquid; must be stored in a freezer to prevent gradual polymerization, which is promoted by mineral and organic acids, bases, aqueous ammonia, strong amines, and heavy metal salts. Stabilizers against polymerization: H2S, alkyl and benzyl thiols, alkyl sulfides, and thioacetamide. Use in a fume hood.
Ethylene sulfide is widely used for mercaptoethylation of primary and secondary amine groups in various organic compounds to obtain aminothiols themselves or to convert them into sulfur heterocycles. Aqueous ammonia causes only a rapid polymerization of ethylene sulfide and no cysteamine formation. The action of anhydrous ammonia has not been investigated. Efforts to obtain monomeric ethylene sulfide addition products to Hydrazine and Hydroxylamine failed.
Weakly basic aryl amines,8 esters of aminobenzoic acids,14 and a-amino acids15 require more drastic conditions (100-105 °C, sealed tube, alcoholic solutions or absence of solvent) for mercaptoethylation.
1. (a) Reynolds, D. D.; Fields, D. L. Chemistry of Heterocyclic Compounds: Heterocyclic Compounds with Three- and Four-Membered Rings; Interscience: New York, 1964; Vol. 19, Part 1, pp 576-623. (b) Sander, M. CRV 1966, 66, 297. (c) Fokin, A. V.; Kolomiets, A. F. Usp. Khim. 1975, 44, 306. (d) Fokin, A. V.; Kolomiets, A. F. Usp. Khim. 1976, 45, 71. (e) Fokin, A. V.; Kolomiets, A. F. Chemistry of Thiiranes; Nauka: Moscow, 1978 (CA 1979, 91, 140 705n). (f) Zoller, U. Chemistry of Heterocyclic Compounds: Small Ring Heterocycles: Aziridines, Azirines, Thiiranes, Thiirenes; Wiley: New York, 1983; Vol. 42, Part 1, pp 333-630.
2. Wineman, R. J.; Gollis, M. N.; James J. C.; Pomponi, A. M. JOC 1962, 27, 4222.
3. (a) The Aldrich Library of FT-IR Spectra; Aldrich Chemical: Milwaukee, 1989; Vol. 3, p 354C. (b) The Aldrich Library of NMR Spectra, 2nd ed.; Aldrich Chemical: Milwaukee, 1983; Vol. 1, p 231C.
4. Golovnya, R. V.; Garbuzov, V. G.; Aerov, A. F. IZV (Engl. Transl.) 1979, 28, 1630.
5. Fieser, L. F.; Fieser, M. FF 1967, 1, 378.
6. Brown, J. R.; Mastromatteo, E. Am. Ind. Hyg. Assoc. J. 1964, 25, 560.
7. Oddon, A.; Wylde J. BSF(2) 1967, 1603.
8. Rachinskii, F. I.; Slavachevskaia, N. M.; Ioffe, D. V. JGU 1958, 28, 3027.
9. Braz, G. I. JGU 1951, 21, 757.
10. Snyder, H. R.; Stewart, J. M.; Ziegler, J. B. JACS 1947, 69, 2672.
11. Marabella, C. P.; Enemark, J. H.; Miller, K. F.; Bruce, A. E.; Pariyadath, N.; Corbin, J. L.; Stiefel E. I. IC 1983, 22, 3456.
12. Karlin, K. D.; Lippard S. J. JACS 1976, 98, 6951.
13. Luhowy, R.; Meneghini, F. JOC 1973, 38, 2405.
14. Yuryev, Yu. K.; Dyatlovitskaya, S. V. JGU 1957, 27, 1855.
15. Bulavin, L. G. JOU 1971, 7, 2168.
16. (a) Bulavin, L. G. JOU 1971, 7, 2703. (b) Corbin, J. L.; Miller, K. F.; Pariyadath, N.; Wherland, S.; Bruce A. E.; Stiefel, E. I. ICA 1984, 90, 41.
17. Rima, G.; Satge, J.; Fatome, M.; Laval, J. D.; Sentenac-Roumanou H.; Lion, C.; Lazraq, M. Eur. J. Med. Chem. 1991, 26, 291.
18. Trujillo, D. A.; McMahon, W. A., Jr.; Lyle, R. E. JOC 1987, 52, 2932.
19. Fokin, A. V.; Kolomiets, A. F.; Rudnitskaya, L. S.; Shevchenko, V. I. IZV(Engl. Transl.) 1975, 24, 582.
20. Fokin, A. V.; Kolomiets, A. F.; Levskaya, G. S. IZV (Engl. Transl.) 1975, 24, 334.
21. Yuryev, Yu. K.; German, L. S. JGU 1955, 25, 2421.
22. Razuvaev, G. A.; Etlis, V. S.; Grobov, L. N. JOU 1963, 33, 1335.
23. Pelletier, S. W.; Nowacki, J.; Mody, N. V. SC 1979, 9, 201.

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