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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:
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.

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

109.4 °F - closed cup

Flash Point(C)

43 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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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