Ferrocene, ethenyl-

Base Information

• Chemical Name: Ferrocene, ethenyl-
• CAS No.: 1271-51-8
• Molecular Formula: C12H12Fe
• Molecular Weight: 212.074
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID00925784
• Mol file: 1271-51-8.mol

Synonyms:Ferrocene, ethenyl-;cyclopenta-1,3-diene;2-ethenylcyclopenta-1,3-diene;iron(2+);VFC;EINECS 215-041-1;DTXSID00925784;AKOS028109484;A805647;iron;1-vinylcyclopenta-1,3-diene

Chemical Property of Ferrocene, ethenyl-

Chemical Property:

• Appearance/Colour: stalline solid
• Vapor Pressure: 10.8mmHg at 25°C
• Melting Point: 51-53 °C(lit.)
• Boiling Point: 80-85 °C/0.2 mm Hg(lit.)
• Flash Point: 62 °C
• PSA: 0.00000
• LogP: 2.59670
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 212.028836
• Heavy Atom Count: 13
• Complexity: 70

Purity/Quality:

98% ^*data from raw suppliers

Vinylferrocene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11-22
• Safety Statements: 16-22-24/25-7/9-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC1=CC=C[CH-]1.[CH-]1C=CC=C1.[Fe+2]
• Uses: Used in the synthesis of 2-aminomethylferrocenes from vinyl ferrocene and lithium amides.

Technology Process of Ferrocene, ethenyl-

There total 71 articles about Ferrocene, ethenyl- 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: 98.0%

ferrocenecarboxaldehyde (12093-10-6) + Methyltriphenylphosphonium bromide (1779-49-3) → vinyl ferrocene (1271-51-8)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; pentane; at 0 ℃; for 0.333333h;

ferrocenecarboxaldehyde; In tetrahydrofuran; pentane; at 20 ℃;

DOI:10.1021/ja413060u

Reference yield: 97.0%

1-ferrocenylethanol (1277-49-2) → vinyl ferrocene (1271-51-8)

Guidance literature:

With copper(II) sulfate; In toluene; byproducts: H2O; in boiling toluene;;

Reference yield: 97.0%

(2-ferrocenylethyl)trimethylammonium iodide → vinyl ferrocene (1271-51-8)

Guidance literature:

With potassium amide; In ammonia;

upstream raw materials:

ferrocene

acrylonitrile

diiron nonacarbonyl

1-ferrocenylethanol

Downstream raw materials:

ferroceneacetylene

1-ferrocenylethanol

acetylferrocene

stilbene

Refernces

• 1、 Yu, Songjie,Noble, Adam,Bedford, Robin B.,Aggarwal, Varinder K.. "Methylenespiro[2.3]hexanes via Nickel-Catalyzed Cyclopropanations with [1.1.1]Propellane". . p. 20325 - 20334. Retrieved 2019.
• 2、 Horspool, W. M.,Sutherland, R. G.. "". . . Retrieved 1966.
• 3、 Hauser et al.. "". . . Retrieved 1958.
• 4、 Hauser, C. R.,Lindsay, J. K.,Lednicer, D.. "". . p. 358 - 361. Retrieved 1958.
• 5、 Singh, Jatinder,Ghosh, Sanjib,Deb, Mayukh,Elias, Anil J.. "Reactions of Cp2TiMe2 with ferrocene and (n5-Cp)Co(n4-C4Ph4) derived esters and amides: A new route for 1-methylvinyl and methyl ketone derived metal sandwich compounds". . p. 85 - 91. Retrieved 2016.
• 6、 Kolyvanov, Nikita A.,Oparina, Ludmila A.,Tarasova, Olga A.,Albanov, Alexander I.,Gusarova, Nina K.,Trofimov, Boris A.. "Pd-catalyzed rearrangement of ferrocenylalkyl vinyl ethers to the related aldehydes and ketones". . . Retrieved 2020.
• 7、 Sasaki, Y.,Pittman, C. U.. "". . p. 3723 - 3726. Retrieved 1973.
• 8、 Kikuchi, Jun,Korenaga, Toshinobu,Obayashi, Ren,Terada, Masahiro,Toda, Yasunori. "Dynamic parallel kinetic resolution of α-ferrocenyl cation initiated by chiral Br?nsted acid catalyst". . p. 10306 - 10312. Retrieved 2021.
• 9、 Ayers, O. E.,Smith, T. G.,Burnett, J. D.,Ponder, B. W.. "". . p. 1606 - 1607. Retrieved 1966.
• 10、 Schloegl,Mohar. "". . p. 376. Retrieved 1961.