Tri-n-butyltin chloride

• Catalog No.: A10746
• CAS Number: 1461-22-9
• M. F.: C12H27ClSn
• M. W.: 325.49678
• Purity: 96%

SYNONYMS

• Title: 三正丁基氯化锡
• IUPAC name: tributylstannylium chloride
• IUPAC Traditional name: tributylstannylium chloride
• Synonyms: Chlorotri-n-butylstannane; Chlorotri-n-butyltin

DATABASE IDS

• EC Number: 215-958-7
• MDL Number: MFCD00000521
• Beilstein Number: 3535715
• CAS Number: 1461-22-9

PROPERTIES

• Purity: 96%
• Boiling Point: 171-173°C/25mm
• Density: 1.200
• Flash Point: 120°C(248°F)
• Melting Point: -19°C
• Refractive Index: 1.4910
• GHS Hazard statements: H301-H312-H315-H319-H372-H400-H410
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P260-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Risk Statements: 21-25-36/38-48/23/25-50/53
• RTECS: WH6820000
• Safety Statements: 36/37/39-45-60-61
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2788
• Packing Group: II

REFERENCES

• Reaction with Grignard or lithium reagents gives alkyl or aryl stannanes.
• Organostannanes undergo the Stille coupling reaction, in the presence of Pd catalysts, such as trans-Dichlorobis(triphenylphosphine)palladium(II), 10491, or Tetrakis(triphenylphosphine)palladium(0), 10548, with aryl halides: Angew. Chem. Int. Ed., 25, 508 (1986); J. Org. Chem., 52, 422 (1987), aryl triflates: J. Am. Chem. Soc., 106, 4630 (1984); 108, 3033 (1986); 109, 5478 (1987); Org. Synth. Coll., 9, 553 (1998), or aryl fluorosulfonates: J. Org. Chem., 56, 3493 (1991). LiCl is added in the reaction with triflates to prevent decomposition of the catalyst. These reactions are of wide scope (coupling also occurs with vinyl, allyl or benzyl halides), take place under very mild conditions, and a variety of other functional groups can be tolerated. For recent reviews of the Stille reaction, see: Adv. Met.-Org. Chem., 5, 1 (1996); Org. React., 50, 1 (1997).
• For use in stannylation of allylic chlorides via the ultrasound-promoted Barbier reaction with Mg, see: Chem. Lett., 1857 (1986); Org. Synth. Coll, 9, 707 (1998). For an example of stannylation of indoles as a route to 2-substituted indoles, see 1-Methylindole, A12605.
• See also: A. G. Davies, Organotin Chemistry, Wiley-VCH, N. Y. (1997); H. Nozaki in Organometallics in Synthesis, M. Schlosser, Ed., Wiley, N.Y. (1994), p535; (reviews): Tetrahedron, 45, 909 (1989); J. Organomet. Chem., 437, 23 (1992).