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87630-35-1 - 1-(Triisopropylsilyl)pyrrole, 95% - TIPS-pyrrole - L13152 - Alfa Aesar

L13152 1-(Triisopropylsilyl)pyrrole, 95%

CAS Number
87630-35-1
Synonyms
TIPS-pyrrole

Size Price ($) Quantity Availability
1g 31.60
5g 93.60
25g 340.00
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1-(Triisopropylsilyl)pyrrole, 95%

MDL
MFCD00054932

Chemical Properties

Formula
C13H25NSi
Formula Weight
223.44
Boiling Point
78°/0.4mm
Flash Point
106°(222°F)
Density
0.904
Refractive Index
1.4920
Sensitivity
Moisture Sensitive
Solubility
Not miscible in water.

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).

Notes

Moisture sensitive. Incompatible with oxidizing agents.

Literature 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-(Phenyl­sulfonyl)­pyrrole, A11599.

GHS Hazard and Precautionary Statements

Hazard Statements: H302

Harmful if swallowed.

Precautionary Statements: P280f

Wear protective clothing.

Other References

Beilstein
3540663
Harmonized Tariff Code
2933.99
TSCA
No

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