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1-(Triisopropylsilyl)pyrrole, 95%, Thermo Scientific Chemicals
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Catalog number L13152.06
also known as L13152-06
Price (USD)/ Each
99.60
-
Quantity:
5 g
Price (USD)/ Each
99.60
1-(Triisopropylsilyl)pyrrole, 95%, Thermo Scientific Chemicals
Catalog numberL13152.06
Price (USD)/ Each
99.60
-
Chemical Identifiers
CAS87630-35-1
IUPAC Name1-[tris(propan-2-yl)silyl]-1H-pyrrole
Molecular FormulaC13H25NSi
InChI KeyFBQURXLBJJNDBX-UHFFFAOYSA-N
SMILESCC(C)[Si](C(C)C)(C(C)C)N1C=CC=C1
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless to yellow to green to brown
FormLiquid
Refractive Index1.4895-1.4955 @ 20?C
Assay (GC)≥94.0%
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 and 3-nitropyrrole, required for the synthesis of 1 -(2?-deoxy-β-D-ribofuranosyl)-3-nitropyrrole. It participates in various electrophilic substitution reactions specifically at β-position, via reaction with various electrophilic reagents (Br+, I+,NO2+,etc).
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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 and 3-nitropyrrole, required for the synthesis of 1 -(2′-deoxy-β-D-ribofuranosyl)-3-nitropyrrole. It participates in various electrophilic substitution reactions specifically at β-position, via reaction with various electrophilic reagents (Br+, I+,NO2+,etc).
Solubility
Not miscible in water.
Notes
Moisture sensitive. Incompatible with oxidizing agents.
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 and 3-nitropyrrole, required for the synthesis of 1 -(2′-deoxy-β-D-ribofuranosyl)-3-nitropyrrole. It participates in various electrophilic substitution reactions specifically at β-position, via reaction with various electrophilic reagents (Br+, I+,NO2+,etc).
Solubility
Not miscible in water.
Notes
Moisture sensitive. Incompatible with oxidizing agents.
RUO – Research Use Only
General References:
- Cristiano Zonta; Fabrizio Fabris; Ottorino De Lucchi. The pyrrole approach toward the synthesis of fully functionalized cup-shaped molecules. Org. Lett. 2005, 7,(6), 1003-1006.
- Izzat T.Raheem; Parvinder S.Thiara; Eric N.Jacobsen . Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions. Org. Lett. 2008, 10,(8), 1577-1580.
- Valuable intermediate in which the bulky TIPS group promotes regioselective 3-substitution. Bromination, nitration and base-catalyzed acylation all occur regioselectively at the 3-position: Tetrahedron Lett., 24, 3455 (1983). Metallating agents also attack at the 3-position: J. Org. Chem ., 55, 6317 (1990); 57, 1653 (1992). The silyl group is easily removed with F -, e.g. TBAF. For a review of synthesis of 3-substituted pyrroles, see: Synthesis, 353 (1985). Compare 1-(Phenyl sulfonyl) pyrrole, A11599.