tributyl(1-ethoxyethenyl)stannane

• ChemBase ID: 64836
• Molecular Formular: C16H34OSn
• Molecular Mass: 361.14156
• Monoisotopic Mass: 362.16315971
• SMILES: C=C(OCC)[Sn](CCCC)(CCCC)CCCC
• Canonical SMILES: CCCC[Sn](C(=C)OCC)(CCCC)CCCC
• InChI: InChI=1S/C4H7O.3C4H9.Sn/c1-3-5-4-2;3*1-3-4-2;/h1,4H2,2H3;3*1,3-4H2,2H3
• InChIKey: HGXJOXHYPGNVNK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tributyl(1-ethoxyethenyl)stannane
• IUPAC Traditional name: tributyl(1-ethoxyethenyl)stannane
• Synonyms: Tributyl(1-ethoxyvinyl)stannane; Tributyl(1-ethoxyvinyl)tin; Tributyl(1-ethoxyvinyl)tin; (1-Ethoxyethenyl)tributylstannane; (1-Ethoxyvinyl)tributylstannane; 1-Ethoxy-1-(tributylstannyl)ethylene 95%; (1-Ethoxyvinyl)tri-n-butylstannane; Tri-n-butyl(1-ethoxyvinyl)tin; 三丁基(1-乙氧基乙烯)锡; 三正丁基(1-乙氧基乙烯基)锡

Database IDs

• CAS Number: 97674-02-7
• MDL Number: MFCD00010240
• PubChem SID: 162030575; 24856628
• PubChem CID: 619414

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.5688
• LogD (pH = 7.4): 7.5688
• Log P: 7.5688
• Molar Refractivity: 88.5829 cm^3
• Polarizability: 35.968628 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Boiling Point: 85-86 °C/0.1 mmHg(lit.); 85-86°C/0.1mm; 85-86°C/0.07mm
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• Density: 1.067; 1.069; 1.069 g/mL at 25 °C(lit.)
• Refractive Index: 1.4760; n20/D 1.476(lit.)

Safety Information

• Storage Warning: IRRITANT; Toxic/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: 35-36/37/39-45-60-61; 36/37/39-45-60-61
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H315-H319-H372-H400-H410; H301-H315-H319-H372-H400
• GHS Precautionary statements: P273-P301 + P310-P305 + P351 + P338-P314; P280-P273-P309-P310-P501A
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2788 6.1/PG 3

Product Information

• Purity: 96%; 97%
• Linear Formula: [CH3(CH2)3]3SnC(OC2H5)=CH2

DETAILS

Sigma Aldrich - 275123

Application
Electrophilic methyl ketone equivalent used in a recent synthesis of a 13-oxophorbine (chlorophyll) from the corresponding 13-bromochlorin.1
Reagent employed in palladium-catalyzed coupling reactions with sulfoxides, α-haloethers, and chlorocyclobutenones. Also used to convert acid chlorides to α-oxygenated enones.
General description
This vinylstannane undergoes Stille coupling with a vinyl triflate, giving, after hydrolysis, an α,β-unsaturated ketone, thus acting as an acetyl anion equivalent.2
Packaging
1, 5, 25, 100 g in glass bottle