TRIBUTYL(1-ETHOXYVINYL)TIN Chemical Properties

Melting point:

<0°C

Boiling point:

85-86 °C0.1 mm Hg(lit.)

Density 

1.069 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.476(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Choroform (Slightly), Ethyl Acetate (Slightly)

form 

liquid

Specific Gravity

1.069

color 

colorless

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C4H7O.3C4H9.Sn/c1-3-5-4-2;3*1-3-4-2;/h1,4H2,2H3;3*1,3-4H2,2H3;

InChIKey

HGXJOXHYPGNVNK-UHFFFAOYSA-N

SMILES

[Sn](CCCC)(CCCC)(CCCC)C(OCC)=C

Safety Information

Hazard Codes 

T,N

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

TSCA 

No

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29319090

MSDS

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

TRIBUTYL(1-ETHOXYVINYL)TIN Usage And Synthesis

Reaction

Versatile tin reagent used for the introduction of a 1-ethoxyvinyl group via a Stille cross-coupling reaction, (palladium-catalyzed coupling of an organohalide (or pseudohalide) with an organotin compound).

Chemical Properties

Clear colorless liquid

Uses

Electrophilic methyl ketone equivalent used in a recent synthesis of a 13-oxophorbine (chlorophyll) from the corresponding 13-bromochlorin.

General Description

This vinylstannane undergoes Stille coupling with a vinyl triflate, giving, after hydrolysis, an α,β?unsaturated ketone, thus acting as an acetyl anion equivalent.

Synthesis

Under nitrogen protection, 112 g of potassium tert-butoxide (1.0 mmol), and 139.2 g of tetramethylethylenediamine (1.2 mmol) were added to 1000 mL of anhydrous hexane and cooled to -30 °C. A 400 mL hexane solution of n-butyllithium (2.5 M) was slowly added dropwise, and the reaction was maintained at -30 °C for 1.5 h after completion of the dropwise addition, followed by cooling to -40 °C. 108 g of vinyl ether (1.5 mmol) was dissolved in 200 mL of anhydrous tetrahydrofuran and slowly added dropwise to the above mixed solution, maintained at -40 °C for 0.5 h. After the reaction was completed, it was warmed up to -20 °C to continue the reaction for 1 h. It was subsequently cooled to -78 °C. 227.9 g of tributyltin chloride (0.7 mmol) was dissolved in 500 mL of anhydrous tetrahydrofuran and slowly added dropwise to the reaction mixture, maintained at -78 °C for 2 hours, followed by natural warming and stirring for 8 hours. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of 400 mL of saturated ammonium chloride solution, filtered and the organic phase was separated. The aqueous phase was extracted with hexane (500 mL x 3), the organic layers were combined and washed sequentially with water (500 mL x 3) and saturated brine (500 mL x 3). The organic phase was dried with 100 g of anhydrous sodium sulfate, filtered and concentrated under reduced pressure to constant weight to give 228.7 g of tributyl(1-ethoxyvinyl)tin crude product. The crude product was subjected to distillation under vacuum and the fraction at 75 °C-85 °C at 0.005 mmHg was collected to give 205 g of colorless transparent liquid in 81.03% yield.

References

[1] Patent: CN106046043, 2016, A. Location in patent: Paragraph 0016; 0017
[2] Organic Process Research and Development, 2014, vol. 18, # 8, p. 993 - 1001

TRIBUTYL(1-ETHOXYVINYL)TIN(97674-02-7)Related Product Information

• 1-Ethoxy-2-(tributylstannyl)ethene
• Zinc trifluoromethanesulfonate
• Homopiperazine
• Tributyl(vinyl)tin
• TRIBUTYL(1-ETHOXYVINYL)TIN
• (1-ETHOXYVINYL)TRIMETHYLSTANNANE
• Tributyltin Hydride
• Ethyltrimethyltin(IV)
• TRIPROPYLTIN
• TETRAMETHYLTIN
• TRI-N-BUTYLMETHYLTIN
• 2-(TRIBUTYLSTANNYL)-5,6-DIHYDRO-[1,4]-DIOXIN
• triethyltin