1-(TRIISOPROPYLSILYL)PYRROLE

1-(TRIISOPROPYLSILYL)PYRROLE Property

Boiling point:

78 °C0.4 mm Hg(lit.)

Density 

0.904 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.492(lit.)

Flash point:

224 °F

storage temp. 

Inert atmosphere,2-8°C

pka

-2.55±0.70(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

0.904

Water Solubility 

Not miscible in water.

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

BRN 

3540663

CAS DataBase Reference

87630-35-1(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

20-22-36

Safety Statements 

24/25-26

WGK Germany 

3

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

1-(TRIISOPROPYLSILYL)PYRROLE Chemical Properties,Usage,Production

Uses

1-(Triisopropylsilyl)pyrrole may be employed as reagent in perfluoroalkylation and Vilsmeier formylation reactions. It may be used in the preparation of:

• ethyl 2-(2,4-dinitrophenylhydrazono]-3-[ 1-(triisopropylsily1)-pyrrol-2-yflpropanoate
• heterocyclic base, 3-nitropyrrole
• 3-nitropyrrole, required for the synthesis of 1 -(2′-deoxy-β-D-ribofuranosyl)-3-nitropyrrole

General Description

1-(Triisopropylsilyl)pyrrole (TISP), a heterocyclic building block, is a pyrrole derivative. TISP has been reported to generate pyrrolic cation radicals during cyclovoltammetric studies, via electroreduction. It participates in various electrophilic substitution reactions specifically at β-position, via reaction with various electrophilic reagents (Br⁺, I⁺,NO₂⁺,etc).

Synthesis

At -78 °C, n-butyllithium (n-BuLi, 1.57 M in n-hexane, 17.3 mL, 27.1 mmol) was slowly added dropwise to a solution of tetrahydrofuran (THF, 36 mL) of pyrrole (1.52 g, 22.6 mmol), and the reaction mixture was kept stirring at -78 °C for 30 min. Subsequently, triisopropylchlorosilane (TIPSCl, 5.3 mL, 24.9 mmol) was added to the reaction mixture and stirring was continued at -78 °C for 5 hours. Upon completion of the reaction, the reaction was quenched by addition of saturated aqueous ammonium chloride (NH4Cl) to the mixture at 0 °C and the mixture was extracted with ethyl acetate (AcOEt). The organic phases were combined and concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was purified by silica gel (SiO2) column chromatography (eluent: n-hexane/ethyl acetate=10:1) to afford 1-(triisopropylmethylsilyl)pyrrole (4.94 g, 98% yield) as a colorless oil.

References

[1] Journal of Natural Products, 2004, vol. 67, # 11, p. 1929 - 1931
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4358 - 4361
[3] Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5504 - 5508
[4] Chemistry - An Asian Journal, 2016, vol. 11, # 7, p. 986 - 990
[5] Tetrahedron, 2008, vol. 64, # 49, p. 11180 - 11184