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'''Acetylferrocene''' is the ] with the formula (C<sub>5</sub>H<sub>5</sub>)Fe(C<sub>5</sub>H<sub>4</sub>COMe). It consists of ] substituted by one ] on one of the ] rings. It is an orange, air-stable solid that is soluble in organic solvents.
'''Acetylferrocene''' is an ] compound based on ] with one ] added to one of the ] rings. It was originally had applications in the military and NASA as an additive in rocket propellant to improve the efficiency of the burning rate. The ferrocenyl derivative has wide applications to biological and medical fields such as ferrocene-modified beta-lactam because of a range of physiological activities, including: anti-malarial, anti-tumor, bactericidal, anti-inflammatory, treatment of anemia, inhibition of enzymatic activity. Acetylferrocene is notable because of its stability, high toxicity, aromaticity, ease for substitution reaction and modification, hydrophobic structure, attacking a variety of enzymes and nucleic acids in cells, and high enzymatic selectivity due to the metallocenal structure. <ref name="use">{{cite web |url=http://watson-int.com/Acetylferrocene_CAS_1271-55-2.html |title=Use of Acetylferrocene |publisher=Watson International Ltd |accessdate=2012-08-06}}</ref> It is typically synthesized from ] and ] in the presence of an acid catalyst such as ] or ].

==Preparation and reactions==
Acetylferrocene is prepared by ] of ferrocene, usually with acetic anhydride]]:<ref>Donahue, C. J., Donahue, E. R., "Beyond Acetylferrocene: The Synthesis and NMR Spectra of a Series of Alkanoylferrocene Derivatives", Journal of Chemical Education 2013, volume 90, pp. 1688. {{DOI|10.1021/ed300544n}}</ref>
:(C<sub>5</sub>H<sub>5</sub><sub>2</sub>)Fe + Ac<sub>2</sub>O → (C<sub>5</sub>H<sub>5</sub>)Fe(C<sub>5</sub>H<sub>4</sub>Ac) + AcOH
The experiment is often used in the instructional laboratory to illustrate acylation as well as chromatographic separations.

Acetylferrocene can be converted to many derivatives, including reduction to the chiral alcohol. The oxidized derivative, acetyl], is used as a 1e-oxidant in the research laboratory.<ref>Connelly, N. G., Geiger, W. E., "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877. {{DOI|10.1021/cr940053x}}</ref>


== References == == References ==

Revision as of 03:10, 23 June 2014

Acetylferrocene
Acetylferrocene
Names
Other names Acetylferrocene
Identifiers
CAS Number
ECHA InfoCard 100.013.676 Edit this at Wikidata
Properties
Chemical formula
Molar mass 228.07 g/mol
Appearance Red brown crystal
Melting point 81–83 °C
Boiling point 161–163 °C (4 mmHg)
Solubility in water Insoluble in water, soluble in most organic solvents
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4 1 0
Lethal dose or concentration (LD, LC):
LD50 (median dose) 25 mg kg (oral, rat)
50 mg kg (oral, mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound
This crystal of acetylferrocene was grown as part of an undergraduate course in UCL’s Department of Chemistry.

Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COMe). It consists of ferrocene substituted by one acetyl group on one of the cyclopentadienyl rings. It is an orange, air-stable solid that is soluble in organic solvents.

Preparation and reactions

Acetylferrocene is prepared by acetylation of ferrocene, usually with acetic anhydride]]:

(C5H52)Fe + Ac2O → (C5H5)Fe(C5H4Ac) + AcOH

The experiment is often used in the instructional laboratory to illustrate acylation as well as chromatographic separations.

Acetylferrocene can be converted to many derivatives, including reduction to the chiral alcohol. The oxidized derivative, acetylferrocenium, is used as a 1e-oxidant in the research laboratory.

References

  1. Sigma-Aldrich Co., Acetylferrocene. Retrieved on 2013-07-20.
  2. http://msds.chem.ox.ac.uk/AC/acetylferrocene.html
  3. https://fscimage.fishersci.com/msds/69220.htm
  4. Donahue, C. J., Donahue, E. R., "Beyond Acetylferrocene: The Synthesis and NMR Spectra of a Series of Alkanoylferrocene Derivatives", Journal of Chemical Education 2013, volume 90, pp. 1688. doi:10.1021/ed300544n
  5. Connelly, N. G., Geiger, W. E., "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877. doi:10.1021/cr940053x
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