275069

Sigma-Aldrich

Ethynyltributylstannane

95%

Synonym(s):
Tributylstannylacetylene
Linear Formula:
HC≡CSn(CH2CH2CH2CH3)3
CAS Number:
Molecular Weight:
315.08
Beilstein/REAXYS Number:
3537659
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

95%

refractive index

n20/D 1.476 (lit.)

bp

70 °C/0.2 mmHg (lit.)

density

1.089 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)C#C

InChI

1S/3C4H9.C2H.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H;

InChI key

YEMJHNYABQHWHL-UHFFFAOYSA-N

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Related Categories

Application

Ethynyltributylstannane can be used as a reactant to prepare:
  • Terminal arylacetylene derivatives by Stille coupling reaction with aryl halides in the presence of palladium catalyst.
  • 1,4-bis(tributylstannyl)but-1-en-3-yne by dimerization using a metal complex having bulky ligand catalyst system.
  • Isoquinolone derivatives by reacting with benzotriazinones via denitrogenative insertion in the presence of nickel catalyst.
  • Enyne key intermediates in the total synthesis of (-)-acutumine and (-)-dechloroacutumine.

Packaging

1, 5 g in glass bottle

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2788 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

165.2 °F - closed cup

Flash Point(C)

74 °C - closed cup

Journal of the Chemical Society. Perkin Transactions 1, 1657-1657 (1993)
Synthesis of terminal arylacetylenes by a Stille coupling reaction catalysed by a MCM-41-supported bidentate phosphine palladium (O) complex
H Wenyan, et al.
J. Chem. Res. (M), 2008(11), 615-618 (2008)
Total Syntheses of (-)-Acutumine and (-)-Dechloroacutumine
King SM, et al.
Angewandte Chemie (International ed. in English), 125(13), 3730-3733 (2013)
Dimerization of terminal alkynes catalyzed by a nickel complex having a bulky phosphine ligand
Ogoshi S, et al.
Chemical Communications (Cambridge, England), 2008(23), 2732-2733 (2004)
Synlett, 557-557 (1994)

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