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Merck
CN

275069

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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24856626
MDL number:
MFCD00009420
Beilstein/REAXYS Number:
3537659

Key Documents

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Product Name

Ethynyltributylstannane, 95%

InChI

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

SMILES string

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

InChI key

YEMJHNYABQHWHL-UHFFFAOYSA-N

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.)

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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.

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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

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

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM3445
SHBB9063V
05696MKV
BCBC5026
BCBC5026V

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Total Syntheses of (-)-Acutumine and (-)-Dechloroacutumine
King SM, et al.
Angewandte Chemie (International ed. in English), 125(13), 3730-3733 (2013)
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)
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)
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