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

L13152 1-(Triisopropylsilyl)pyrrole, 95%

Codice CAS
87630-35-1
Sinonimi
TIPS-pyrrole

Dimensioni Prezzo ($) Quantità Disponibilità
1g 31,60
5g 93,60
25g 340,00
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1-(Triisopropylsilyl)pyrrole, 95%

MDL
MFCD00054932

Proprietà chimiche

Formula
C13H25NSi
Peso formula
223.44
Punto di ebollizione
78°/0.4mm
Punto di infiammabilità
106°(222°F)
Densità
0.904
Indice di rifrazione
1.4920
Sensibilità
Moisture Sensitive
Solubilità
Not miscible in water.

Applicazioni

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).

Note

Moisture sensitive. Incompatible with oxidizing agents.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302

Harmful if swallowed.

Dichiarazioni precauzionali: P260u-P201-P280h-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310a-P405-P501a

Obtain special instructions before use. Wear protective gloves/clothing. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3540663
Codice tariffe armonizzato
2933.99
TSCA
No

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