1. Organotin Compounds Robert Ono 4 December 2012

2. Organotin Uses Protodehalogenation Cross-Coupling (Stille)

3. Trialkyltin Chlorides Size of R Reactivity decreaseincrease Toxicity Example: SnMe 3 Cl vs. SnBu 3 Cl LD 50 12.6 mg/kg 129 mg/kg(NaCN LD 50 : 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 R 3 Sn-X byproducts from your reactions ( + SnR 3 -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.