2-(TRIBUTYLSTANNYL)THIOPHENE

2-(TRIBUTYLSTANNYL)THIOPHENE Property

Melting point:

197-198 °C

Boiling point:

155 °C/0.1 mmHg (lit.)

Density 

1.175 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.518(lit.)

Flash point:

221 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

liquid

color 

Clear, almost colourless

Specific Gravity

1.175

InChI

InChI=1S/C4H3S.3C4H9.Sn/c1-2-4-5-3-1;3*1-3-4-2;/h1-3H;3*1,3-4H2,2H3;

InChIKey

UKTDFYOZPFNQOQ-UHFFFAOYSA-N

SMILES

[Sn](CCCC)(CCCC)(CCCC)C1SC=CC=1

CAS DataBase Reference

54663-78-4(CAS DataBase Reference)

Safety

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 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H372Causes damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-(TRIBUTYLSTANNYL)THIOPHENE Chemical Properties,Usage,Production

Chemical Properties

Colorless liquid

Uses

2-(Tri-n-butylstannyl)thiophene derivative is employed in Stille reaction involving efficient carbon-carbon bond formation.

Uses

2-(Tributylstannyl)thiophene has been used to synthesize diphenylquinoxaline monomer for the electrochromism polymers. It can also be used as a reactant in Stille coupling reaction.

Synthesis

2-Bromothiophene (4.89 g, 30 mmol) and 60 mL of anhydrous tetrahydrofuran were added to a 250 mL three-necked flask with a device constant pressure dropping funnel. The system was evacuated and then displaced three times with argon to remove air. The reaction flask was placed in a cryostat reaction bath and cooled to -20 °C. Subsequently, a n-hexane solution of n-butyllithium (2.2 mol/L, 15 mL, 33 mmol) was slowly added dropwise under argon protection and the temperature was maintained at -20 °C for 1 h of reaction. Next, tributyltin chloride (8.95 mL, 33 mmol) was slowly added dropwise and the reaction was continued at -20 °C for 1 hour. Upon completion of the reaction, the reaction system was slowly brought to room temperature and stirred overnight. After the reaction was terminated, 150 mL of deionized water was added to the reaction flask and extracted three times with dichloromethane (80 mL x 3). The organic layers were combined and washed three times with saturated saline (100 mL x 3). The organic phase was dried overnight over anhydrous magnesium sulfate and filtered to remove the desiccant. The filtrate was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography using a petroleum ether solution containing a small amount of triethylamine as eluent to give 11.08 g of the colorless liquid product 2-tributylmethylstannylthiophene in 90% yield.

References

[1] Patent: CN105732680, 2016, A. Location in patent: Paragraph 0021