2-(Trimethylsilyl)pyridine Chemical Properties

Boiling point:

47-49 °C5 mm Hg(lit.)

Density 

0.9113 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.489(lit.)

Flash point:

126 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

6.62±0.10(Predicted)

Specific Gravity

0.911

color 

Colorless to Almost colorless

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

Sensitive 

Light Sensitive

InChI

InChI=1S/C8H13NSi/c1-10(2,3)8-6-4-5-7-9-8/h4-7H,1-3H3

InChIKey

IBLKFJNZUSUTPB-UHFFFAOYSA-N

SMILES

C1([Si](C)(C)C)=NC=CC=C1

CAS DataBase Reference

13737-04-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36-37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

2-(Trimethylsilyl)pyridine Usage And Synthesis

Uses

2-Trimethylsilylpyridine is a pyridine derivative that can be used as an intermediate in organic synthesis.

Chemical Properties

Clear colorless to brown liquid

Synthesis

A solution of 2-chloropyridine (20.7 mL, 217 mmol) and trimethylchlorosilane (28.0 mL, 221 mmol) in THF (100 mL) was added dropwise to a rapidly stirred mixture of magnesium chips (6.75 g, 281 mmol) in THF (175 mL). The solution in was added dropwise to a rapidly stirred mixture of magnesium shavings (6.75 g, 281 mmol) in THF (175 mL). After adding approximately 10 mL of solution was followed by the addition of diiodomethane (0.2 mL), then iodine pellets, and then isopropylmagnesium chloride (2.0 M THF solution, 1 mL, 2 mmol). The suspension was then carefully heated to reflux and the remaining chloride solution was added dropwise over 2.75 hours. The reaction was then allowed to cool to room temperature and stirred overnight. Approximately 200 mL of was removed by distillation of the THF and benzene (125mL) was added. The suspension was refluxed for 2 hours and the benzene was decanted. The benzene was then removed by adding more benzene (2 x 125 mL), refluxing (1 each time) and decanting. hours) and decanting the process was repeated and the combined benzene fractions were concentrated in vacuum and distilled to give 2-trimethylsilylpyridine (6.97 g, 46.2 mmol , 21%) in colorless liquid form.

2-(Trimethylsilyl)pyridine(13737-04-7)Related Product Information

• 2,4,6-Collidine
• Vinyltrimethoxysilane
• 4-Methylpyridine
• N-(Trimethylsilyl)acetamide
• Benzyltrimethylammonium chloride
• 2-Chloro-5-chloromethylpyridine
• Trimethylamine hydrochloride
• Azamethiphos
• Pyridine
• 2,3,5-Collidine
• 2,6-Lutidine
• Trimethylsilylacetylene
• Behentrimonium Chloride
• 4-Cyano-3-(trimethylsilyl)pyridine,3-(TRIMETHYLSILYL)PYRIDINE-4-CARBONITRILE
• 5,6-Difluoro-4-(trimethylsilyl)pyridine-2-carboxylic acid
• Silicone rubber,methyl-vinyl
• 3-Fluoro-2-(trimethylsilyl)pyridine
• 3-Chloro-2-(trimethylsilyl)-pyridine