Ketone, ferrocenyl phenyl (8CI)

Base Information

• Chemical Name: Ketone, ferrocenyl phenyl (8CI)
• CAS No.: 1272-44-2
• Deprecated CAS: 36344-08-8,38960-44-0
• Molecular Formula: C17H14FeO
• Molecular Weight: 290.145
• Hs Code.: 29319090
• Mol file: 1272-44-2.mol

Synonyms:Ketone, ferrocenyl phenyl (8CI);cyclopenta-1,3-diene;cyclopenta-1,3-dien-1-yl(phenyl)methanone;iron(2+);Benzoylferrocen;EINECS 215-054-2;AKOS015916264;B0886;D88711

Chemical Property of Ketone, ferrocenyl phenyl (8CI)

Chemical Property:

• Appearance/Colour: red to red-brown powder
• Vapor Pressure: 0.00311mmHg at 25°C
• Melting Point: 105-107 °C(lit.)
• Refractive Index: 1.597
• Boiling Point: 283.7°C at 760 mmHg
• Flash Point: 118.7°C
• PSA: 17.07000
• Density: 1.117g/cm³
• LogP: 3.29360
• Water Solubility.: Insoluble in water
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 290.039401
• Heavy Atom Count: 19
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

Benzoylferrocene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [CH-]1C=CC=C1.[CH-]1C=CC=C1C(=O)C2=CC=CC=C2.[Fe+2]
• Uses: Intermediate. Reactant for:Deprotonative metalation of ferrocenesOxidative chemistryReduction of ferrocenyl ketonesPolymerization of C-ferrocenyl-substituted phosphaalkeneReactant for synthesis of:Planat chiral triferrocenylmethane derivativeChiral ferrocenyl alcohols via asymmetric transfer hydrogenation

Technology Process of Ketone, ferrocenyl phenyl (8CI)

There total 41 articles about Ketone, ferrocenyl phenyl (8CI) 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: 96.0%

bis(ferrocenyl)mercury (1274-09-5) + benzoyl chloride (98-88-4) → benzoylferrocene (1272-44-2)

Guidance literature:

With NaI; dichloro bis(acetonitrile) palladium(II); In acetone; Fe-complex, ligand, NaI were dissolved in acetone under Ar, Pd-complex was added, stirred at room temp. for 0.5 h; passed through silica, evapd. in vac., column chromy. on silica with benzene;

DOI:10.1016/S0022-328X(01)00979-2

Reference yield: 94.0%

ferrocene (102-54-5,55404-68-7) + benzoyl chloride (98-88-4) → benzoylferrocene (1272-44-2)

Guidance literature:

With aluminium chloride; In dichloromethane; ferrocene (1.0 equiv.) added to a stirred suspension of benzoyl chloride(1.1 equiv.) and aluminium chloride (1.1 equiv.) in dichloromethane, st irred at room temp. overnight (16 h); washed with water, organic layer passed through a plug of alumina, washed with chloroform, washings concentrated in vacuo, crude product purified by flash column chromy. on silica gel (TLC Rf 0.34 (1:3 ether-hexane)), elem. anal.;

DOI:10.1039/b000833h

Reference yield: 89.0%

ferrocenylcopper + benzoyl chloride (98-88-4) → ferrocene (102-54-5,55404-68-7) + benzoylferrocene (1272-44-2) + 1,1''-biferrocene

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; benzoyl chloride is added to suspension of ferrocenylcopper in THF under argon, mixt. is stirred for 1.5 h, treated with NH4OH, stirred for 10 min; addn. of benzene, sepn. of organic layer, washing (water), solvent is distilled off (vac.), chromy. (alumina), elution (petroleum ether, petroleum ether-ether);

upstream raw materials:

diiron nonacarbonyl

ferrocene

phthalic anhydride

homophthalic anhydride

Downstream raw materials:

ferrocene

Refernces

• 1、 Chen, Chao,Froehlich, Roland,Kehr, Gerald,Erker, Gerhard. "Structural features of lithio[3]ferrocenophane systems bearing stabilizing dimethylamino substituents". . p. 3248 - 3253. Retrieved 2008.
• 2、 Salisova, M.,Toma, S.,Solcaniova, E.. "FRIEDEL-CRAFTS ALKYLATIONS OF FERROCENE WITH UNSATURATED LACTONES, SOME UNUSUAL REACTIONS CAUSED BY THE Β-FERROCENYLCARBENIUM ION". . p. 77 - 84. Retrieved 1987.
• 3、 Sollott,Peterson. "". . p. 1506. Retrieved 1969.
• 4、 Plevová, Kristína,Kisszékelyi, Péter,Vargová, Denisa,Andrej?ák, Samuel,Tóth, Viktor,Fertá?, Luká?,Rakovsky, Erik,Filo, Juraj,?ebesta, Radovan. "Diastereoselective Double C?H Functionalization of Chiral Ferrocenes with Heteroaromatics". supporting information. p. 15501 - 15507. Retrieved 2021/10/07.
• 5、 Marijan, Marijan,Juri?, Sandra,Mihali?, Zlatko,Kronja, Olga. "Impact of the α-Ferrocenyl Group on the Solvolytic Reactivity – Electrofugality – of Ferrocenylphenylmethyl Cations". . p. 537 - 546. Retrieved 2018/12/11.