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Organotin Compounds

Organotin Compounds. Robert Ono 4 December 2012. Organotin Uses. Protodehalogenation. Cross-Coupling ( Stille ). Trialkyltin Chlorides. Size of R. Reactivity. decrease. increase. Toxicity. Example:. SnMe 3 Cl vs. SnBu 3 Cl. LD 50 12.6 mg/kg 129 mg/kg.

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Organotin Compounds

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  1. Organotin Compounds Robert Ono 4 December 2012

  2. Organotin Uses • Protodehalogenation • Cross-Coupling (Stille)

  3. Trialkyltin Chlorides Size of R Reactivity decrease increase Toxicity Example: SnMe3Cl vs. SnBu3Cl LD50 12.6 mg/kg 129 mg/kg (NaCN LD50: 4.8 mg/kg)

  4. Toxicity • Ingestion, inhalation, or skin exposure • Skin, eye irritation • Neurotoxin • Accumulates in parts of the brain • Dizzyness, vertigo, memory loss, aggressiveness… • Reproductive toxicity in lab animals • Not really carcinogenic • Also,

  5. Handling • Proper PPE • Protect eyes, hands, skin • Chlorides – avoid contact with moisture • Hydrides – handle under inert gas atmosphere • Disposal: • Wash contaminated equipment with organic solvent, into container, tag for pickup • Same for small spills (larger spills, call EHS)

  6. How to get rid of R3Sn-X byproducts from your reactions ( + SnR3-Br or Cl) • Vigorously stir crude reaction mixture (in organic solvent) with 1M NaOH for 1h • Separate organic phase, filter through silica • R3Sn-X is converted to polar R3Sn-OH, which does not elute on silica gel Tetrahedron Lett. 1998 , 39 , 2123.

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