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.)

Flash point:

165 °F

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

liquid

Specific Gravity

1.089

Appearance

Colorless to light yellow Liquid

Water Solubility 

Not miscible or difficult to mix with water.

Sensitive 

Moisture Sensitive

BRN 

3537659

InChI

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

InChIKey

YEMJHNYABQHWHL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

994-89-8(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

F 

21

TSCA 

No

HazardClass 

6.1

PackingGroup 

III

HS Code 

29319090

Storage Class

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

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

TRIBUTYLSTANNYLACETYLENE Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

Used to prepare vinylstannanes and stannylisoxazoles. Ethynylation reagent for azaaromatics.

Uses

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.

Purification Methods

Purify 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(994-89-8)Related Product Information

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