1-(Triisopropylsilyl)pyrrole

Base Information

• Chemical Name: 1-(Triisopropylsilyl)pyrrole
• CAS No.: 87630-35-1
• Molecular Formula: C13H25NSi
• Molecular Weight: 223.434
• Hs Code.: 2933990090
• Mol file: 87630-35-1.mol

Synonyms:1-(Triisopropylsilyl)-1H-pyrrole;1-(Triisopropylsilyl)pyrrole;N-(Triisopropylsilyl)pyrrole;

Chemical Property of 1-(Triisopropylsilyl)pyrrole

Chemical Property:

• Vapor Pressure: 0.00643mmHg at 25°C
• Refractive Index: n20/D 1.492(lit.)
• Boiling Point: 271.5 °C at 760 mmHg
• PKA: -2.55±0.70(Predicted)
• Flash Point: 106.7 °C
• PSA: 4.93000
• Density: 0.86 g/cm³
• LogP: 4.51170
• Storage Temp.: Room temperature.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Not miscible in water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(Triisopropylsilyl)pyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20-22-36
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 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). 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-yflpropanoateheterocyclic base, 3-nitropyrrole3-nitropyrrole, required for the synthesis of 1 -(2′-deoxy-β-D-ribofuranosyl)-3-nitropyrrole

Technology Process of 1-(Triisopropylsilyl)pyrrole

There total 10 articles about 1-(Triisopropylsilyl)pyrrole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

pyrrole (109-97-7,30604-81-0) + triisopropylsilyl chloride (13154-24-0) → N-triisopropylsilylpyrrole (87630-35-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/np0498399

Reference yield: 86.0%

→ (E)-methyl 3-methoxy-2-(N-methylpyrrol-3-yl)propenoate (114078-42-1) + N-triisopropylsilylpyrrole (87630-35-1)

Guidance literature:

Reference yield: 74.8%

3-bromo-1-triisopropylsilanyl-1H-pyrrole (87630-36-2) + (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene (108030-46-2) → N-triisopropylsilylpyrrole (87630-35-1) + (E,E)-1-triisopropylsilyl-3-(4-nitro-1,3-butadienyl)pyrrole

Guidance literature:

3-bromo-1-triisopropylsilanyl-1H-pyrrole; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.333333h;

(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.3987/COM-00-8859

upstream raw materials:

pyrrole

triisopropylsilyl chloride

potassium pyrrolide

3-bromo-1-triisopropylsilanyl-1H-pyrrole

Downstream raw materials:

2-(4-methylbenzenesufinyl)-1H-pyrrole

3-(p-tolylsulfinyl)-1-(triisopropylsilyl)pyrrole

ethyl pyrrolo[1,2-c]pyrimidine-3-carboxylate

1H-Pyrrolo<3,2-c>pyridin-6-carbonsaeure-ethylester

Refernces

• 1、 Barnes,Hu,Hunt. "Electrophilic fluorination of a highly functionalized pyrrole". . p. 1749 - 1755. Retrieved 1994.
• 2、 Andrieux, Claude P.,Audebert, Pierre,Hapiot, Phillipe,Saveant, Jean-Michel. "Observation of the Cation Radicals of Pyrrole and of Some Substituted Pyrroles in Fast-Scan Cyclic Voltammetry. Standard Potentials and Lifetimes". . p. 2439 - 2440. Retrieved 1990.
• 3、 Andrieux, Claude P.,Audebert, Pierre,Hapiot, Philippe,Saveant, Jean-Michel. "Identification of the First Steps of the Electrochemical Polymerization of Pyrroles by Means of Fast Potential Step Techniques". . p. 10158 - 10164. Retrieved 1991.
• 4、 Hu, Ji'an,Kou, Jingping,Li, Jianbing,Li, Yanhua,Lin, Biyue,Wang, Zhongqing,Wu, Shuming,Xiao, Qingbo,Xin, Libo,Zhou, Xinglin,Zhu, Zhu. "Identification, characterization, synthesis of major metabolites biotransformed from vonoprazan fumarate". . . Retrieved 2022/02/10.
• 5、 Nagy, Sándor,Szigetvári, áron,Ilkei, Viktor,Krámos, Balázs,Béni, Zoltán,Szántay, Csaba,Hazai, László. "Synthesis of aminal-type Lilium candidum alkaloids and lilaline; determination of their relative configuration by the concerted use of NMR spectroscopy and DFT conformational analysis". . . Retrieved 2021/01/25.