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271438

Sigma-Aldrich

Tributyl(vinyl)tin

97%

Synonym(s):

Tributyl(vinyl)stannane, Tributylstannylethylene, Vinyltributylstannane

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About This Item

Linear Formula:
CH2=CHSn[CH3(CH2)3]3
CAS Number:
7486-35-3
Molecular Weight:
317.10
Beilstein/REAXYS Number:
3537662
EC Number:
231-291-4
MDL number:
MFCD00009421
UNSPSC Code:
12352103
PubChem Substance ID:
24856437
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.478 (lit.)

bp

104-106 °C/3.5 mmHg (lit.)

density

1.085 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/3C4H9.C2H3.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H,2H2;

InChI key

QIWRFOJWQSSRJZ-UHFFFAOYSA-N

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General description

Tributyl(vinyl)tin is an organostannane, commonly used in the palladium-catalyzed cross coupling reactions.

Application

Vinyl nucleophile for bromoacetylenes and bromoaromatics.

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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

109.4 °F - closed cup

flash_point_c

43 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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The Journal of Organic Chemistry, 59, 7164-7164 (1994)
New synthetic applications of organotin compounds: synthesis of stereodefined 2-iodo-2-alkenones, 2-substituted (E)-2-alkenones and 2-methyl-2-cycloalkenones
Fabio B et al.
Tetrahedron, 49, 4677-4698 (1993)
Ernesto G Occhiato et al.
Journal of medicinal chemistry, 47(14), 3546-3560 (2004-06-25)
New 5alpha-reductase 1 (5alphaR-1) inhibitors were designed to complete a consistent set of analogues suitable for a 3D QSAR study. These compounds were synthesized by a modification of the aza-Robinson annulation, further functionalized by Pd-catalyzed cross-coupling processes, and were tested
Masahiro Yoshida et al.
Organic letters, 6(12), 1979-1982 (2004-06-05)
[reaction: see text] A novel type of cascade ring expansion process has been developed by the palladium-catalyzed reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. The reaction proceeds in a stereospecific manner to produce (Z)-2-(3-aryl-1-propenyl)cyclopentanones. It has also been found that regioselective
R Skoda-Földes et al.
Steroids, 60(12), 812-816 (1995-12-01)
Direct and carbonylative coupling reactions of various steroid derivatives possessing iodo- and bromo-alkenyl moiety (17-iodo-androst-16-ene, 1, 17-bromoandrost-2,16-diene, 2, 17-iodo-4-aza-4-methylandrost-16-en-3-one, 3, 17-iodo-4-azaandrost-16-en-3-one, 4) with vinyltributylstannane and ethynyltributylstannane were carried out in the presence of various palladium catalysts. While carbonylation took place

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