| Company Name: |
Energy Chemical |
| Tel: |
400-0056266 |
| Email: |
sales8178@energy-chemical.com |
|
| | 3-Bromo-1-(triisopropylsilyl)pyrrole Basic information |
| | 3-Bromo-1-(triisopropylsilyl)pyrrole Chemical Properties |
| Boiling point | 100 °C(Press: 0.1 Torr) | | density | 1,16 g/cm3 | | refractive index | n20/D1.519 | | Fp | >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) |
| | 3-Bromo-1-(triisopropylsilyl)pyrrole Usage And Synthesis |
| 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 |
| | 3-Bromo-1-(triisopropylsilyl)pyrrole Preparation Products And Raw materials |
|