TRIBUTYLSTANNYLACETYLENE

TRIBUTYLSTANNYLACETYLENE Basic information
Product Name:TRIBUTYLSTANNYLACETYLENE
Synonyms:Ethynyltri-n-butylstannane~Tri-n-butyl(ethynyl)tin~Tri-n-butylstannylacetylene;Ethynyltri-n-butyltin,97%;TRI-N-BUTYLETHYNYLTIN;TRI-N-BUTYLSTANNYLACETYLENE;TRIBUTYLSTANNYLACETYLENE;TRIBUTYLETHYNYLSTANNANE;TRIBUTYL(ETHYNYL)TIN;Tributylethynylstannane,98%
CAS:994-89-8
MF:C14H28Sn
MW:315.08
EINECS:628-819-4
Product Categories:organic tin;Stannanes;Acetylenes;Classes of Metal Compounds;Functionalized Acetylenes;Sn (Tin) Compounds;Typical Metal Compounds
Mol File:994-89-8.mol
TRIBUTYLSTANNYLACETYLENE Structure
TRIBUTYLSTANNYLACETYLENE Chemical Properties
Boiling point 70 °C0.2 mm Hg(lit.)
density 1.089 g/mL at 25 °C(lit.)
refractive index n20/D 1.476(lit.)
Fp 165 °F
storage temp. Sealed in dry,Store in freezer, under -20°C
Specific Gravity1.089
Water Solubility Not miscible or difficult to mix with water.
Sensitive Moisture Sensitive
BRN 3537659
InChIKeyYEMJHNYABQHWHL-UHFFFAOYSA-N
CAS DataBase Reference994-89-8(CAS DataBase Reference)
Safety Information
Hazard Codes T,N,Xn
Risk Statements 21-25-36/38-48/23/25-50/53
Safety Statements 35-36/37/39-45-60-61
RIDADR UN 2788 6.1/PG 3
WGK Germany 3
21
TSCA No
HazardClass 6.1
PackingGroup III
HS Code 29319090
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
TRIBUTYLSTANNYLACETYLENE Usage And Synthesis
Chemical Propertiesclear colorless liquid
UsesUsed to prepare vinylstannanes and stannylisoxazoles. Ethynylation reagent for azaaromatics.
UsesEthynyltributylstannane 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.

Purification MethodsPurify it by dissolving the reagent (ca 50g) in heptane (250mL), washing it with H2O (100mL), drying (MgSO4), evaporating and distilling in a vacuum. It has IR: max 3280 ( C), 2950, 2850, 2005 (CC), 1455, 1065 and 865cm-1. [Bottaro et al. J Org Chem 46 5221 1981, Stille & Simpson J Am Chem Soc 109 2138 1987, Zavgorodnii et al. J Gen Chem USSR (Engl Edn) 37 1469 1967.]
TRIBUTYLSTANNYLACETYLENE Preparation Products And Raw materials
Preparation ProductsETHYL 5-TRIBUTYLSTANNANYLISOXAZOLE-3-CARBOXYLATE-->4,4'-DIETHYNYLBIPHENYL-->1-BROMO-2-ETHYNYLBENZENE-->Cyanoacetylene
Tributyltin chloride Acetylenedicarboxylic acid Dimethyl acetylenedicarboxylate GALLIUM(III) TRIFLUOROMETHANESULFONATE Scandium trifluoromethanesulfonate YTTERBIUM(III) TRIFLUOROMETHANESULFONATE HYDRATE 2-Ethynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane Diethyl acetylenedicarboxylate TRIBUTYLSTANNYLACETYLENE 1-TRIBUTYLSTANNYL-2-TRIMETHYLSILYLACETYLENE PHENYLETHYNYLTRI-N-BUTYLTIN Acetylene TRIBUTYL(1-PROPYNYL)TIN BIS(TRI-N-BUTYLSTANNYL)ACETYLENE

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