2-(TRIBUTYLSTANNYL)PYRIDINE

2-(TRIBUTYLSTANNYL)PYRIDINE Property

Melting point:

132-135 °C

Boiling point:

134 °C

Density 

1.15

refractive index 

1.5130

Flash point:

>110°C

storage temp. 

-20°C

pka

5.21±0.19(Predicted)

form 

liquid

Specific Gravity

1.142

color 

Clear, yellow

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

BRN 

479329

Exposure limits

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

InChIKey

GYUURHMITDQTRU-UHFFFAOYSA-N

CAS DataBase Reference

17997-47-6(CAS DataBase Reference)

Safety

Hazard Codes 

T,Xi,N

Risk Statements 

21-25-36/38-48/23/25-50/53-10

Safety Statements 

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

RIDADR 

2788

WGK Germany 

3

Hazard Note 

Toxic

TSCA 

No

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

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

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

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.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

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

Uses

Building block in an efficient, palladium-catalyzed synthesis of 2-pyridylazaazulene, a bidentate ligand showing pH and cationic-metal dependent emission spectra.

Synthesis

General procedure for the preparation of 2-tributylmethyltin alkylpyridine by the reaction of 2-bromopyridine with tributyltin chloride: butyllithium (2.5 M hexane solution, 6.33 mmol) was added dropwise to a solution of freshly distilled 2-bromopyridine (1 g, 6.33 mmol) in tetrahydrofuran (12 mL) at -78 °C and degassed. After stirring for 30 minutes, tributyltin chloride (1.7 mL, 6.33 mmol) was added to the slightly reddish solution and stirring was continued at -78 °C for 1 hour, then brought to room temperature and stirred for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride solution and extracted with diethyl ether. The organic phase was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 20/1) to afford the target product 2-tributylmethylstannylpyridine in 94% yield.1H NMR (CDCl3) δ (ppm): 8.73 (dtd, J = 4.9,1.9,1.0,1H,H6), 7.48 (dt, J = 7.4,1.8,1H,H5). 7.39 (dt, J = 7.4,1.6,1H, H3), 7.10 (ddd, J = 6.9,4.9,1.7,1H, H4), 1.70-1.05 (m, 18H, CH2), 0.85 (t, 9H, J = 7.3, CH3).

References

[1] Patent: US2013/296302, 2013, A1. Location in patent: Paragraph 0592
[2] Patent: US2014/194441, 2014, A1. Location in patent: Paragraph 0455
[3] Inorganic Chemistry, 2013, vol. 52, # 9, p. 5570 - 5580
[4] Patent: US9219237, 2015, B1. Location in patent: Page/Page column 11
[5] European Journal of Inorganic Chemistry, 2002, # 3, p. 573 - 579