hexabutyldistannane

• ChemBase ID: 146412
• Molecular Formular: C24H54Sn2
• Molecular Mass: 580.08756
• Monoisotopic Mass: 582.22693973
• SMILES: CCCC[Sn](CCCC)(CCCC)[Sn](CCCC)(CCCC)CCCC
• Canonical SMILES: CCCC[Sn]([Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC
• InChI: InChI=1S/6C4H9.2Sn/c6*1-3-4-2;;/h6*1,3-4H2,2H3
• InChIKey: REDSKZBUUUQMSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hexabutyldistannane
• IUPAC Traditional name: hexabutyldistannane
• Synonyms: Bis(tri-n-butyltin); Hexa-n-butyldistannane; Hexa-n-butylditin; Hexabutyldistannane; Hexabutylditin; Bis(tributyltin); Hexabutyldistannane; 六正丁基二锡; 六正丁基锡; 双(三丁基锡); 六正丁基二锡

Database IDs

• CAS Number: 813-19-4
• EC Number: 212-383-3
• MDL Number: MFCD00009417
• Beilstein Number: 3605476
• PubChem SID: 24874160; 162240609; 24855108
• PubChem CID: 6327815

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.7898
• LogD (pH = 7.4): 7.7898
• Log P: 7.7898
• Molar Refractivity: 117.7554 cm^3
• Polarizability: 55.613953 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Boiling Point: 197-198°C/10mm
• Flash Point: 124°C(255°F); 130 °C; 266 °F
• Density: 1.148 g/mL at 25 °C(lit.); 1.152
• Refractive Index: 1.5120; n20/D 1.512(lit.); n20/D 1.513

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2788; UN2788
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 36/37/39-45-60-61
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H315-H319-H372-H400-H410; H301-H312-H315-H319-H372-H410
• GHS Precautionary statements: P260-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P273-P280-P301 + P310-P305 + P351 + P338-P314-P501
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2788 6.1/PG 3

Product Information

• Purity: ≥95% (GC); 95%; 98%
• Grade: technical
• Linear Formula: (CH3CH2CH2CH2)3SnSn(CH2CH2CH2CH3)3

DETAILS

Sigma Aldrich - 251127

Application
Reagent used to stannylate aryl halides for subsequent Stille coupling.1 Also used in the radioiodination of styrlpyridines.2
Packaging
10, 50 g in glass bottle

Sigma Aldrich - 52070

Other Notes
Initiator of various radical reactions1,2,3,4

REFERENCES

• Source of on thermolysis or photolysis of tributylstannyl radicals, avoiding the problems sometimes attributable to the hydrogen donor capability of Tri-n-butyltin hydride, A13298.ɑ-Iodo ketones or esters with a suitably-placed double bond undergo radical cyclizations on UV irradiation in the presence of a catalytic amount of the distannane: Tetrahedron Lett., 28, 2477 (1987); J. Org. Chem., 54, 1826, 3140 (1989). Compare analogous reductive cyclizations using the tin hydride. Improved conditions have been developed for generation of the tributylstannyl radical by mild UV irradiation in the presence of a triplet sensitizer (e.g. 4'-Methoxyacetophenone, A11162), allowing selective C-C bond forming reactions to be performed under free-radical conditions: Synlett, 287 (1993).
• Brings about the deoxygenation of amine oxides: Synthesis, 55 (1987), and the photo-desulfurization of 1,3-dithiole-2-thiones to tetrathiafulvalenes: J. Am. Chem. Soc., 98, 7440 (1976).