tributylstannane

• ChemBase ID: 6209
• Molecular Formular: C12H27Sn
• Molecular Mass: 290.04378
• Monoisotopic Mass: 291.11346986
• SMILES: C(C[Sn](CCCC)CCCC)CC
• Canonical SMILES: CCCC[Sn](CCCC)CCCC
• InChI: InChI=1S/3C4H9.Sn/c3*1-3-4-2;/h3*1,3-4H2,2H3
• InChIKey: PIILXFBHQILWPS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tributylstannane
• IUPAC Systematic name: Tributylstannane
• IUPAC Traditional name: tributyltin
• Synonyms: tributylstannanyl; Tributyltin hydride; Tributylstannane; Tributylstannyl hydride; Tributyltin hydride solution; TBTH; Tri-n-butylstannane; Tri-n-butyltin hydride; Tributyltin hydride; 三丁基氢化锡; 三丁基氢化锡 溶液; 三正丁基氢化锡

Database IDs

• CAS Number: 688-73-3
• EC Number: 211-704-4
• MDL Number: MFCD00009416
• Beilstein Number: 3587329
• PubChem SID: 24854056; 24889424; 99445072; 160969634
• PubChem CID: 3032732; 5948
• CHEBI ID: 27086
• Chemspider ID: 5734
• Gmelin ID: 4258
• MeSH Name: Tributyltin
• Wikipedia Title: Tributyltin_hydride

CALCULATED PROPERTIES

ALOGPS 2.1

• Log P: 6.17
• LOG S: -3.52
• Solubility (Water): 8.82e-02 g/l

JChem

• Log P: 3.2027
• Molar Refractivity: 59.2157 cm^3
• Polarizability: 28.1632 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.2027
• LogD (pH = 7.4): 3.2027

PROPERTIES

Physical Property

• Solubility: Slowly reacts in water
• Melting Point: 0-1°C
• Boiling Point: 68-74°C/0.3mm; 80 °C/0.4 mmHg(lit.); 80°C (at 50 Pa)
• Flash Point: 104 °F; -15 °C; 40 °C; 40°C(104°F); 5 °F
• Density: 0.895 g/mL at 25 °C; 1.082 g cm^-3; 1.082 g/mL at 25 °C(lit.); 1.098
• Refractive Index: 1.4730; n20/D 1.438; n20/D 1.473(lit.)

Safety Information

• Storage Warning: Air & Moisture Sensitive
• RTECS: WH8675000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T)
• UN Number: 1993; UN2929
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 2; 3; II
• Risk Statements: 10-21-25-36/38-48/23/25-50/53; 11-21-25-36/38-48/23/25-50/53-65-67
• Safety Statements: 16-26-33-36/37-45-60-61-62; 26-36/37-45-61; 35-36/37/39-45-60-61; 36/37/39-45-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H301-H312-H315-H319-H372-H410; H301-H312-H315-H319-H372-H226-H400-H410; H301-H312-H315-H319-H372-H410
• GHS Precautionary statements: P273-P280-P301 + P310-P305 + P351 + P338-P314-P501; P280-P273-P305+P351+P338-P309-P310-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2; UN 1993 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (GC); 97%
• Concentration: 1 M in cyclohexane
• Grade: purum
• Contains: 0.05% BHT as stabilizer
• Linear Formula: [CH3(CH2)3]3SnH
• Empirical Formula (Hill Notation): C12H28Sn

DETAILS

DrugBank - DB08601

Drug information: experimental

Sigma Aldrich - 234788

Application
A widely used radical reagent used in reductive cleavage,1 radical dehalogenation, and intramolecular radical cyclization.2
Radical promoted intramolecular cyclization leading to isoxazolo-benzaulene ring system. Vinyl tin fragment used in a synthesis of (+)-panepophenanthrin via biomimetic Diels-Alder dimerization.
Packaging
10 g in glass bottle
50, 500 g in Sure/Seal™

Sigma Aldrich - 704091

Packaging
10, 50 mL in glass bottle
Application
Reactant or reagent for:
• Alkyne hydrostannations1
• Intramolcular cyclization for the synthesis of zoanthamine alkaloids2
• Stereoselective C-glycosylation of pyranosides using Heck allylation3
• Synthesis of phenylbutenoid dimers for use in treating diseases4
• Preparation of N-acyl derivatives of ecteinascidin 7705
• Syntehsis of cyclonucleosides using black light induced radical cyclization6

Sigma Aldrich - 90915

Other Notes
Reducing agent acting via radical intermediates1,2,3,4

REFERENCES

• Reducing agent and source of tributyltin radicals. Widely used for selective reduction of alkyl halides to alkanes by a radical chain mechanism. The reaction is tolerant of a wide range of functionality, including OH and NH, in contrast to polar metal hydride reagents. For reviews, see: Synthesis, 499 (1970); 665 (1987). For a brief feature on uses of this reagent in synthesis, see: Synlett, 173 (2007). For use in the synthesis of deoxy sugars via reductive rearrangement of glycosyl bromides, see: Org. Synth. Coll., 8,583 (1993). Cyclization of the initially-formed alkyl radical to a suitably positioned double bond may occur. Formation of 5-membered rings is strongly favoured, and ring closure onto an existing ring gives the cis-fused product. See, e.g.: J. Am. Chem. Soc., 108, 5893 (1986):
  
• Intermolecular coupling with electron-deficient alkenes is also effective: Angew. Chem. Int. Ed., 23, 69 (1984); Org. Synth. Coll., 8, 148 (1993). Review: Synthesis, 417 (1988).
• Secondary alcohols can be deoxygenated by reduction of their xanthate derivatives: J. Chem. Soc., Perkin 1, 1574 (1975); Org. Synth. Coll., 7, 139 (1990), avoiding the rearrangements encountered with carbocation-based methods.
• TBTH also cleaves other C-heteroatom bonds, controlled by the stability of the resulting radical: Nitro-groups at tertiary centers are readily cleaved: Synthesis, 693 (1986). Azides are readily reduced to amines: Synlett, 342 (1991). C-S and C-Se bonds are also cleaved. J. Am. Chem. Soc., 104, 2046 (1982); 112, 4008 (1990); J. Org. Chem., 49, 5206 (1984); 54, 1234 (1989).
• Dialdehydes and keto aldehydes undergo free-radical intramolecular pinacol coupling to give cyclic diols: J. Am. Chem. Soc., 117, 7283 (1995); J. Org. Chem., 63, 6357 (1998).
• For generation and use of tributylstannyllithium, see: Org. Synth. Coll., 8, 562 (1993). Hydroxymethylation of TBTH occurs with LDA and paraformaldehyde. Subsequent reaction with dimethoxymethane gives the hydroxymethyl anion equivalent tributyl[(methoxymethoxy)methyl]stannane: Org. Synth. Coll., 9, 493, 704 (1998).
• Arylstannanes have been produced by Pd-catalyzed coupling with aryl iodides: Synlett, 1064 (2000).
• Free-radical hydrostannylation of alkenes occurs with TBTH to give alkylstannanes. The reaction is catalyzed by, e.g. Rh complexes: Chem. Lett., 881 (1988), or Pd complexes: Angew. Chem. Int. Ed., 35, 1329 (1996), and refs therein. Syn-addition to alkynes gives vinylstannanes, useful intermediates which undergo electrophilic substitution reactions with retention of configuration. Thus, iodine, NIS and NBS give vinyl halides: J. Org. Chem., 47, 404 (1982); Tetrahedron, 42, 3575 (1986), and alkyllithium compounds exchange to give vinyllithiums: J. Am. Chem. Soc., 99, 7365 (1977). Intramolecular reaction with a double bond has been used in cyclization reactions: Org. Synth. Coll., 8, 381 (1993):