tributylstannylium chloride

• ChemBase ID: 295173
• Molecular Formular: C12H27ClSn
• Molecular Mass: 325.49678
• Monoisotopic Mass: 326.08232254
• SMILES: CCCC[Sn+](CCCC)CCCC.[Cl-]
• Canonical SMILES: CCCC[Sn+](CCCC)CCCC.[Cl-]
• InChI: InChI=1S/3C4H9.ClH.Sn/c3*1-3-4-2;;/h3*1,3-4H2,2H3;1H;/q;;;;+1/p-1
• InChIKey: GCTFWCDSFPMHHS-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 1461-22-9
• EC Number: 215-958-7
• MDL Number: MFCD00000521
• Beilstein Number: 3535715
• PubChem SID: 180680704
• PubChem CID: 9927325

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.5287
• LogD (pH = 7.4): 3.5287
• Log P: 3.5287
• Molar Refractivity: 58.4157 cm^3
• Polarizability: 27.806976 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -19°C
• Boiling Point: 171-173°C/25mm
• Flash Point: 120°C(248°F)
• Density: 1.200
• Refractive Index: 1.4910

Safety Information

• RTECS: WH6820000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: UN2788
• Hazard Class: 6.1
• Packing Group: II
• Risk Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 36/37/39-45-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Hazard statements: H301-H312-H315-H319-H372-H400-H410
• GHS Precautionary statements: P260-P301+P310-P305+P351+P338-P302+P352-P405-P501A

Product Information

• Purity: 96%

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).