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95085

Sigma-Aldrich

Tributyl(vinyl)stannane

purum, ≥97.0% (GC)

Synonym(s):

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:
329770417
NACRES:
NA.22

grade

purum

Quality Level

100

assay

≥97.0% (GC)

form

liquid

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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Other Notes

Reagent used for the Pd-catalyzed Stille cross-coupling vinylation [1][2][3][4];

signalword

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG2157

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V. Farina et al.
J. Org. React., 50, 1-1 (1998)
A.M. Echavarren, J.K. Stille
Journal of the American Chemical Society, 110, 1557-1557 (1988)
Karsten Menzel et al.
Journal of the American Chemical Society, 125(13), 3718-3719 (2003-03-27)
This communication describes a significant expansion in the scope of Stille reactions of Csp3-X electrophiles, specifically, that Pd/P(t-Bu)2Me catalyzes the room-temperature cross-coupling of a variety of functionalized, beta-hydrogen-containing alkyl bromides with an array of alkenyltin reagents. The structure of the
W.J. Scott et al.
Accounts of Chemical Research, 21, 47-47 (1988)
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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