ChemicalBook > CAS DataBase List > 1-(TRIISOPROPYLSILYL)PYRROLE

1-(TRIISOPROPYLSILYL)PYRROLE

Product Name
1-(TRIISOPROPYLSILYL)PYRROLE
CAS No.
87630-35-1
Chemical Name
1-(TRIISOPROPYLSILYL)PYRROLE
Synonyms
DK940;DKSI181;TIPS-pyrrole;N-TRIISOPROPYLSILYL PYRROLE;1-(TRIISOPROPYLSILYL)PYRROLE;1-TRIISOPROPYLSILANYL-1H-PYRROLE;1-(Triisopropylsilyl)pyrrole 95%;1-(Triisopropylsilyl)-1H-pyrrole;Tri-iso-propyl(pyrrol-1-yl)silane;tri(propan-2-yl)-pyrrol-1-ylsilane
CBNumber
CB1250712
Molecular Formula
C13H25NSi
Formula Weight
223.43
MOL File
87630-35-1.mol
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1-(TRIISOPROPYLSILYL)PYRROLE Property

Boiling point:
78 °C0.4 mm Hg(lit.)
Density 
0.904 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.492(lit.)
Flash point:
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
CAS DataBase Reference
87630-35-1(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
20-22-36
Safety Statements 
24/25-26
WGK Germany 
3
HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
377945
Product name
1-(Triisopropylsilyl)pyrrole
Purity
95%
Packaging
5ml
Price
$98.03
Updated
2025/07/31
Sigma-Aldrich
Product number
377945
Product name
1-(Triisopropylsilyl)pyrrole
Purity
95%
Packaging
25ml
Price
$164.18
Updated
2025/07/31
TCI Chemical
Product number
T1677
Product name
1-(Triisopropylsilyl)pyrrole
Purity
>96.0%(GC)
Packaging
5mL
Price
$105
Updated
2025/07/31
TCI Chemical
Product number
T1677
Product name
1-(Triisopropylsilyl)pyrrole
Purity
>96.0%(GC)
Packaging
25mL
Price
$338
Updated
2025/07/31
TRC
Product number
T895720
Product name
1-(Triisopropylsilyl)pyrrole
Packaging
100mg
Price
$75
Updated
2021/12/16
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1-(TRIISOPROPYLSILYL)PYRROLE Chemical Properties,Usage,Production

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
  • 3-nitropyrrole, required for the synthesis of 1 -(2′-deoxy-β-D-ribofuranosyl)-3-nitropyrrole

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

Preparation Products

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1-(TRIISOPROPYLSILYL)PYRROLE Suppliers

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View Lastest Price from 1-(TRIISOPROPYLSILYL)PYRROLE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
1-(TRIISOPROPYLSILYL)PYRROLE 87630-35-1
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11

87630-35-1, 1-(TRIISOPROPYLSILYL)PYRROLERelated Search:

4-BROMO-1-(TRIISOPROPYLSILYL)-1H-INDOLE 5-BROMO-1-(TRIISOPROPYLSILYL)-1H-INDOLE 3-Pinacolateboryl-1H-pyrrole 1-(TRIISOPROPYLSILYL)PYRROLE-3-BORONIC ACID 1-(TRIISOPROPYLSILYL)PYRROLE Sodium 5-[(4-Amino-1-naphthyl)azo]-2-[4-[(2-hydroxy-1-naphthyl)azo]-2-sulfonatostyryl]benzenesulfonate Triisopropylsilane 3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE 3-IODO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE 5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE 5-FLUORO-3-IODO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE 1-(TRIISOPROPYLSILYL)INDOLE 3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE,3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE 95+% 5-IODO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE CHEMBRDG-BB 4011733 5-FLUORO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-(TRIISOPROPYLSILYL)-1H-INDOLE 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-(TRIISOPROPYLSILYL)-1H-INDOLE

  • 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
  • TIPS-pyrrole
  • Tri-iso-propyl(pyrrol-1-yl)silane
  • 1-[Tris(1-Methylethyl)silyl]-1H-pyrrole
  • tri(propan-2-yl)-pyrrol-1-ylsilane
  • <font color="#ff0000">87630-35-1</font>
  • DK940
  • DKSI181
  • 87630-35-1
  • 87630-35-0
  • C13H24NSi
  • Trimethylsilylazide, etc.
  • Si (Classes of Silicon Compounds)
  • Reagents for Conducting Polymer Research
  • Pyrroles (for Conduting Polymer Research)
  • Heterocyclic Building Blocks
  • Pyrroles
  • Si-N Compounds
  • Building Blocks
  • 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