全氯甲硫醇

全氯甲硫醇是化学式 CCl3SCl的有机硫化合物，主要用于合成染料和抗真菌剂盖普丹和灭菌丹（英语：folpet）。它是无色且难闻刺鼻的油状液体，不过商购的样本呈黄色。它不溶于水，可溶于有机溶剂。全氯甲硫醇其实是一种硫基氯（英语：sulfenyl chloride），不是硫醇。 1915年，法国在香槟战役中把全氯甲硫醇用作化学武器，但很快就因为容易被发现、分解和去除而被淘汰。 全氯甲硫醇是由Rathke于1873年通过氯气和二硫化碳反应发现的，此方法至今仍用于生产全氯甲硫醇。这个反应由碘或氯化氢催化。 CS2 + 3 Cl2 → CCl3SCl + SCl2 2 CS2 + 5 Cl2 → 2 CCl3SCl + S2Cl2 它也可以由氯化二甲硫醚或硫光气而成。 全氯甲硫醇会缓慢水解： CSCl4 + 2 H2O → CO2 + 4 HCl + 1⁄8 S8 它会被硝酸氧化，生成三氯甲磺酰氯（Cl3CSO2Cl），这是一种白色固体。它在140 °C的二甲苯和三氯化铁催化下用锡或9,10-二氢蒽脱氯，可以合成硫光气。 全氯甲硫醇会和氟化汞或氟化银发生卤素交换反应，生成二氯氟甲硫基氯（CCl2FSCl），后者可用来合成抗真菌剂苯氟磺胺（德语：Dichlofluanid）和对甲抑菌灵（德语：Tolylfluanid）。 全氯甲硫醇可通过呼吸道、皮肤或口服吸收。它会刺激眼睛、喉咙、支气管和肺泡，也会导致肝脏和肾脏损伤。对大鼠和小鼠的动物实验表明全氯甲硫醇是剧毒，中毒症状有腹泻、皮肤刺激以及呼吸急促。 Record of Trichlormethylsulfenylchlorid in the GESTIS Substance Database from the IFA（英语：Institute for Occupational Safety and Health） Douglass, Irwin B.; Martin, Frederic T.; Addor, Roger. Sulfenyl Chloride studies. II. Mono-, Di-, and Tri-Chloromethanesulfenyl Chlorides and Certain of their Derivatives. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1951, 16 (8): 1297–1302. ISSN 0022-3263. doi:10.1021/jo50002a018.  Rogers, Max T.; Gross, K. J. The Electric Moments of Some Sulfur and Selenium Compounds. Journal of the American Chemical Society (American Chemical Society (ACS)). 1952, 74 (21): 5294–5296. ISSN 0002-7863. doi:10.1021/ja01141a018.  NIOSH Pocket Guide to Chemical Hazards. #0489. NIOSH.  Perchloromethyl mercaptan. Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).  Committee on Acute Exposure Guideline Levels, Committee on Toxicology, National Research Council, (2011), Acute Exposure Guideline Levels for Selected Airborne Chemicals. Sosnovsky, George. The Chemistry Of Trichloromethanesulfenyl Chloride. Chemical Reviews (American Chemical Society (ACS)). 1958, 58 (3): 509–540. ISSN 0009-2665. doi:10.1021/cr50021a003.  Autenrieth, W.; Hefner, Heinrich. Über Versuche mit Thiophosgen. Berichte der deutschen chemischen Gesellschaft (A and B Series) (Wiley). 1925-10-14, 58 (9): 2151–2156. ISSN 0365-9488. doi:10.1002/cber.19250580935.  Prakash, G.K.Surya; Hu, Jinbo; Simon, Jurgen; Bellew, Donald R.; Olah, George A. Preparation of α,α-difluoroalkanesulfonic acids. Journal of Fluorine Chemistry (Elsevier BV). 2004, 125 (4): 595–601. ISSN 0022-1139. doi:10.1016/j.jfluchem.2003.11.031.  Patent Schering DE 416603. James, J. William. XXIX.—The action of chlorine on organic thiocyanates. Part I. Methyl thiocyanate. J. Chem. Soc., Trans. (Royal Society of Chemistry (RSC)). 1887, 51 (0): 268–274. ISSN 0368-1645. doi:10.1039/ct8875100268.  Klason, Peter. Ueber einige schwefelhaltige Derivate des Kohlensäureesters. Berichte der deutschen chemischen Gesellschaft (Wiley). 1887, 20 (2): 2384–2385. ISSN 0365-9496. doi:10.1002/cber.18870200256.  Greco, C., (1978), Production of perchloromethyl mercaptan, Stauffer ChemicalCompany, Westport, Conn. Dyson, G. M. (1926). "Thiophosgene". Org. Synth. 6: 86.  K. T. Potts, C. Sapino. Thiocarbonyl halides. S. Patai (编). Acyl Halides. PATAI'S Chemistry of Functional Groups. 1972: 349–380. ISBN 9780470771273. doi:10.1002/9780470771273.ch11.  E. F. Orwoll, US-Patent 2668853. Kober, E.: A New Class of Sulfenyl Derivatives; Perhalogenated Aliphatic Sulfenyl Fluorides in J. Am. Chem. Soc. 81 (1959) 4810–4812, doi:10.1021/ja01527a016. Ham, N.S.: Dichlorofluoromethanesulfenyl chloride in J. Am. Chem. Soc. 83 (1961) 751–752, doi:10.1021/ja01464a052. Fritze, Jürgen. Die ärztliche Begutachtung Rechtsfragen, Funktionsprüfungen, Beurteilungen ; mit 208 Tabellen. Darmstadt. 2008: 296. ISBN 978-3-7985-1563-5. OCLC 199205123 （德语）.  Toxicology and Applied Pharmacology. Vol. 42, S. 417, 1977. Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku, Marhold, J.V., Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha, Czechoslovakia, S. 13, 1972. Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure, Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, S. 97, 1982. National Technical Information Service. Vol. OTS0533569. CID 11666 from PubChem CDC - NIOSH Pocket Guide to Chemical Hazards （页面存档备份，存于互联网档案馆）