3-(1,1,1-TRIBUTYLSTANNYL)PYRIDINE Chemical Properties

Boiling point:

132°C 0,3mm

Density 

1,15 g/cm³

Flash point:

110 °C

storage temp. 

-20°C

form 

liquid

pka

5.21±0.12(Predicted)

Specific Gravity

1.150

color 

Dark brown

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

Exposure limits

ACGIH: TWA 0.1 mg/m3; STEL 0.2 mg/m3 (Skin)
NIOSH: IDLH 25 mg/m3; TWA 0.1 mg/m3

Safety Information

Hazard Codes 

T,Xi,N

Risk Statements 

20/21/22-36/37/38-50/53-48/23/25-36/38-25-21

Safety Statements 

26-36/37/39-61-60-45-35

RIDADR 

UN 2788 6.1/PG 3

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT, KEEP COLD, TOXIC

HazardClass 

6.1

HS Code 

29333990

3-(1,1,1-TRIBUTYLSTANNYL)PYRIDINE Usage And Synthesis

Uses

3-Tributylstannylpyridine (CAS# 59020-10-9) can be used to prepare polyimide material that is resistant to atomic oxygen.

Synthesis

In a two-necked round-bottomed flask 0.5 mL (5.19 mmol) of 3-bromopyridine was dissolved in 25 mL of anhydrous ether and the reaction system was cooled to -78 °C. 3.89 mL (6.23 mmol) of n-butyllithium (1.6 M hexane solution) was slowly added dropwise and the reaction was stirred for 3 hours keeping the temperature at -78 °C. Subsequently, 1.55 mL (5.71 mmol) of tributyltin chloride was added and stirring was continued at -78°C for 30 minutes, then gradually warmed to room temperature and stirred for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ether. The organic layer was separated, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. Purification by column chromatography (eluent: hexane/ethyl acetate=9:1, v/v) afforded 1.58 g of the target product 3-(1,1,1-tributylmethylstannyl)pyridine as a clear oil (yield: 83%).

References

[1] Patent: KR2015/142709, 2015, A. Location in patent: Paragraph 0441-0443
[2] Patent: US6498159, 2002, B1
[3] Patent: US6599917, 2003, B1
[4] Tetrahedron, 2013, vol. 69, # 2, p. 902 - 909
[5] Advanced Synthesis and Catalysis, 2017, vol. 359, # 5, p. 832 - 840

3-(1,1,1-TRIBUTYLSTANNYL)PYRIDINE(59020-10-9)Related Product Information

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