3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE

3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE Property

Boiling point:

100 °C(Press: 0.1 Torr)

Density 

1,16 g/cm³

refractive index 

n20/D1.519

Flash point:

>110℃

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

pka

-5.67±0.70(Predicted)

color 

Black

InChI

InChI=1S/C13H24BrNSi/c1-10(2)16(11(3)4,12(5)6)15-8-7-13(14)9-15/h7-12H,1-6H3

InChIKey

CNAUTMPRKBSDLH-UHFFFAOYSA-N

SMILES

N1([Si](C(C)C)(C(C)C)C(C)C)C=CC(Br)=C1

CAS DataBase Reference

87630-36-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

HS Code 

2933.99.9701

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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

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

Uses

3-Bromo-1-(triisopropylsilyl)pyrrole is a pyrrole analogue mainly used in the field of organic synthesis. It can be used to prepare other heterocyclic compounds such as 1-(triisopropylsilyl)pyrrole and 3-Butadienyl-1-tosylpyrroles.

Synthesis

General procedure for the synthesis of 3-bromo-1-(triisopropylmethylsilyl)pyrrole from 1-(triisopropylmethylsilyl)pyrrole: at -78 °C, N-bromosuccinimide (NBS, 3.25 g, 18.3 mmol) was slowly added to a 1-(triisopropylmethylsilyl)pyrrole (3.72 g, 16.6 mmol) solution of tetrahydrofuran (THF, 17 mL ) solution was maintained at temperature and stirred continuously for 5 hours. Upon completion of the reaction, hexane (15 mL) and pyridine (0.5 mL) were added to the mixture and stirring was continued for 5 minutes. Subsequently, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=30:1) to finally obtain 3-bromo-1-(triisopropylmethylsilyl)pyrrole (4.67 g, 93% yield) as a colorless oil.

References

[1] Chemische Berichte, 1989, vol. 122, p. 169 - 174
[2] Tetrahedron, 2011, vol. 67, # 35, p. 6673 - 6678
[3] Journal of Organic Chemistry, 1984, vol. 49, # 17, p. 3239 - 3240
[4] Tetrahedron, 2004, vol. 60, # 34, p. 7141 - 7146
[5] Organic Letters, 2014, vol. 16, # 24, p. 6334 - 6337