5-(Trimethylsilyl)-1,3-cyclopentadiene

Base Information

• Chemical Name: 5-(Trimethylsilyl)-1,3-cyclopentadiene
• CAS No.: 3559-74-8
• Molecular Formula: C8H14Si
• Molecular Weight: 138.285
• Hs Code.: 29310099
• NSC Number: 176274
• DSSTox Substance ID: DTXSID50947996
• Nikkaji Number: J265.510A
• Mol file: 3559-74-8.mol

Synonyms:5-trimethylsilylcyclopentadiene

Chemical Property of 5-(Trimethylsilyl)-1,3-cyclopentadiene

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 1.75mmHg at 25°C
• Melting Point: -19 °C
• Refractive Index: n20/D 1.465
• Boiling Point: 150.2 °C at 760 mmHg
• Flash Point: 29.7 °C
• PSA: 0.00000
• Density: 0.83 g/cm³
• LogP: 2.82080
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 138.086476981
• Heavy Atom Count: 9
• Complexity: 136

Purity/Quality:

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

Trimethylsilylcyclopentadiene, 97% (mixture of isomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 23-24/25-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)C1C=CC=C1
• Description: Cyclopentadienyltrimethylsilane (also known as trimethylsilyl cyclopentadiene) is a kind of organosilicon compound. It is used in the synthesis of some metal cyclopentadienyl complexes and has attracted interest for its structure owing to its property undergoing rapid sigmatropic rearrangement. It is a useful reactant involved in numerous reactions such as Diels-Alder reactions, synthesis of ring-functionalized molybdenocene complexes, allyl isomerization, aromatization of C5 rings and synthesis of N-hydroxyindoles via nucleophilic addition.
• Uses: Reactant involved in:? ;Diels-Alder reactions1,2? ;Synthesis of ring-functionalized molybdenocene complexes3? ;Allyl isomerization4? ;Aromatization of C5 rings5? ;Synthesis of N-hydroxyindoles via nucleophilic addition6 Reactant involved in:Diels-Alder reactionsSynthesis of ring-functionalized molybdenocene complexesAllyl isomerizationAromatization of C5 ringsSynthesis of N-hydroxyindoles via nucleophilic addition

Technology Process of 5-(Trimethylsilyl)-1,3-cyclopentadiene

There total 3 articles about 5-(Trimethylsilyl)-1,3-cyclopentadiene 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: 57.0%

chloro-trimethyl-silane (75-77-4) + potassium cyclopentadienide (30994-24-2) → trimethylsilylcyclopentadiene (3559-74-8) + 5,5-bis(trimethylsilyl)cyclopentadiene (33630-76-1)

Guidance literature:

DOI:10.1021/ja00533a023

Reference yield: 35.0%

chloro-trimethyl-silane (75-77-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → trimethylsilylcyclopentadiene (3559-74-8) + 5,5-bis(trimethylsilyl)cyclopentadiene (33630-76-1)

Guidance literature:

cyclopenta-1,3-diene; With lithium; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

chloro-trimethyl-silane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.02.087

Reference yield:

chloro-trimethyl-silane (75-77-4) + sodium cyclopentadienide → trimethylsilylcyclopentadiene (3559-74-8) + 5,5-bis(trimethylsilyl)cyclopentadiene (33630-76-1)

Guidance literature:

DOI:10.1039/DT9800001156

upstream raw materials:

chloro-trimethyl-silane

potassium cyclopentadienide

cyclopenta-1,3-diene

Downstream raw materials:

(1R,2R,6S,7S,10S)-1-Methyl-4-phenyl-10-trimethylsilanyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

(1S,2S,6R,7S,10S)-8-Methyl-4-phenyl-10-trimethylsilanyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

(diphenylselenonio)cyclopentadienide

4,4a,5,7a-tetrahydro-3-phenyl-5-(trimethylsilyl)cyclopent-1,2-oxazine

Refernces

• 1、 Cardoso, Ana M.,Clark, Robin J. H.,Moorhause, Stephen. "REACTIONS OF TRIMETHYLSILYLCYCLOPENTADIENE DERIVATIVES WITH TITANIUM, NIOBIUM, AND TANTALUM HALIDES". . p. 1156 - 1160. Retrieved 2007/10/02.