1-(TRIISOPROPYLSILYL)PYRROLE CAS 87630-35-1
1-(TRIISOPROPYLSILYL)PYRROLE Basic information
| Product Name: | 1-(TRIISOPROPYLSILYL)PYRROLE |
| Synonyms: | 1-TRIISOPROPYLSILANYL-1H-PYRROLE;1-(TRIISOPROPYLSILYL)PYRROLE;N-TRIISOPROPYLSILYL PYRROLE;tri(propan-2-yl)-(1-pyrrolyl)silane;1-[tris(propan-2-yl)silyl]-1H-pyrrole;1-(Triisopropylsilyl)pyrrole 95%;1H-Pyrrole, 1-[tris(1-Methylethyl)silyl]-;1-(Triisopropylsilyl)-1H-pyrrole |
| CAS: | 87630-35-1 |
| MF: | C13H25NSi |
| MW: | 223.43 |
| EINECS: | |
| Product Categories: | Pyrrole&Pyrrolidine&Pyrroline;Functional Materials;Pyrroles (for Conduting Polymer Research);Reagents for Conducting Polymer Research;Si (Classes of Silicon Compounds);Si-N Compounds;Trimethylsilylazide, etc.;Building Blocks;Heterocyclic Building Blocks;Pyrroles |
| Mol File: | 87630-35-1.mol |
1-(TRIISOPROPYLSILYL)PYRROLE Chemical Properties
| Boiling point | 78 °C0.4 mm Hg(lit.) |
| density | 0.904 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 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 |
| InChI | 1S/C13H25NSi/c1-11(2)15(12(3)4,13(5)6)14-9-7-8-10-14/h7-13H,1-6H3 |
| InChIKey | FBQURXLBJJNDBX-UHFFFAOYSA-N |
| SMILES | CC(C)[Si](C(C)C)(C(C)C)n1cccc1 |
| CAS DataBase Reference | 87630-35-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20-22-36 |
| Safety Statements | 24/25-26 |
| WGK Germany | 3 |
| HS Code | 2933998090 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 |
| Uses | 1-(Triisopropylsilyl)pyrrole may be employed as reagent in perfluoroalkylation and Vilsmeier formylation reactions. It may be used in the preparation of:
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| 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 | 109-97-7 13154-24-0 87630-35-1 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 |
1-(TRIISOPROPYLSILYL)PYRROLE Preparation Products And Raw materials
| Raw materials | Pyrrole-->Triisopropylsilyl chloride-->Hexane-->Tetrahydrofuran-->n-Butyllithium |
| Preparation Products | NSC 87241-->1-(Triisopropylsilyl)pyrrole-3-boronic acid-->1-(Triisopropylsilyl)pyrrole-3-carbaldehyde-->3-Chloro-1-[tris(1-methylethyl)silyl]-1H-pyrrole |
