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275069

Sigma-Aldrich

Ethynyltributylstannane

95%

Synonym(s):

Tributylstannylacetylene

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About This Item

Linear Formula:
HC≡CSn(CH2CH2CH2CH3)3
CAS Number:
994-89-8
Molecular Weight:
315.08
Beilstein:
3537659
MDL number:
MFCD00009420
UNSPSC Code:
12352103
PubChem Substance ID:
24856626
NACRES:
NA.22

Assay

95%

form

liquid

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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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.

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

165.2 °F - closed cup

Flash Point(C)

74 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM3445
SHBB9063V
05696MKV
BCBC5026
BCBC5026V

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Acta Chemica Scandinavica, 48, 61-61 (1994)
Synlett, 557-557 (1994)
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)
Journal of the Chemical Society. Perkin Transactions 1, 1657-1657 (1993)
Total Syntheses of (-)-Acutumine and (-)-Dechloroacutumine
King SM, et al.
Angewandte Chemie (International ed. in English), 125(13), 3730-3733 (2013)
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