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Sigma-Aldrich

Tributyl(1-ethoxyvinyl)tin

97%

Synonym(s):

(1-Ethoxyvinyl)tri-n-butylstannane

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About This Item

Linear Formula:
[CH3(CH2)3]3SnC(OC2H5)=CH2
CAS Number:
97674-02-7
Molecular Weight:
361.15
MDL number:
MFCD00010240
UNSPSC Code:
12352103
PubChem Substance ID:
24856628
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.476 (lit.)

bp

85-86 °C/0.1 mmHg (lit.)

density

1.069 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)C(=C)OCC

InChI

1S/C4H7O.3C4H9.Sn/c1-3-5-4-2;3*1-3-4-2;/h1,4H2,2H3;3*1,3-4H2,2H3;

InChI key

HGXJOXHYPGNVNK-UHFFFAOYSA-N

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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.

Application

Electrophilic methyl ketone equivalent used in a recent synthesis of a 13-oxophorbine (chlorophyll) from the corresponding 13-bromochlorin.
Reagent employed in palladium-catalyzed coupling reactions with sulfoxides, α-haloethers, and chlorocyclobutenones. Also used to convert acid chlorides to α-oxygenated enones.

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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Journal of the American Chemical Society, 114, 1412-1412 (1992)
Joydev K Laha et al.
The Journal of organic chemistry, 71(18), 7049-7052 (2006-08-26)
A new route to 13(1)-oxophorbines, the parent macrocycle of chlorophylls, begins with the synthesis of a 13-bromochlorin. Pd-mediated coupling of the latter with tributyl(1-ethoxyvinyl)tin and subsequent acidic hydrolysis afforded the 13-acetylchlorin (1). Treatment of 1 with NBS afforded the 15-bromo
Younggi Choi et al.
The Journal of organic chemistry, 69(11), 3758-3764 (2004-05-22)
2-Azabicyclo[2.2.2]oct-5-enes bearing an endo alkenyl substituent were synthesized by Diels-Alder addition of methyl vinyl ketone to a 1,6-dihydropyridine derived from methyl nicotinate. Although 1,5-dienes with this skeleton were unreactive under thermal conditions, they were photochemically reactive. Irradiation of these dienes
Tetrahedron Letters, 34, 2429-2429 (1993)
Tetrahedron Letters, 33, 4885-4885 (1992)
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