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{{Chembox |
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| verifiedrevid = 445590380 |
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| verifiedrevid = 454070258 |
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| ImageFile = Acetylferrocene.gif |
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| ImageFile1 = Acetylferrocene.svg |
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| ImageSize = 150px |
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| ImageSize1 = 150px |
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| ImageFile2 = Crystals of acetylferrocene.jpg |
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| ImageAlt = Acetylferrocene |
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| IUPACName = |
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| ImageSize2 = 150px |
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| ImageAlt = Acetylferrocene |
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| IUPACName = Acetylferrocene |
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| OtherNames = Acetylferrocene |
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| OtherNames = Acetylferrocene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1271-55-2 |
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| PubChem = |
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| CASNo = 1271-55-2 |
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| ChemSpiderID = 21241939 |
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| SMILES = }} |
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| EINECS = 215-043-2 |
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| Section2 = {{Chembox Properties |
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| PubChem = 10857189 |
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| Formula = |
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| RTECS = OB3700000 |
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| MolarMass = 228.07 |
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| InChI=1S/C7H7O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-5H,1H3;1-5H; |
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| Appearance = Red brown crystal |
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| InChIKey = PHMAOJNZIFULOG-UHFFFAOYSA-N |
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| Density = |
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| SMILES = CC(=O)11.11. |
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| MeltingPt = 81-83 °C<ref name="sigma">{{SigmaLink |
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}} |
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| Productgroup = Aldrich |
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|Section2={{Chembox Properties |
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| Productcode = 106860 |
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| Formula = |
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| Accessdate = may 16, 2011}}</ref> |
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| MolarMass = 228.07 g/mol |
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| BoilingPt = 161 - 163 °C (4 mmHg) |
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| Appearance = Red brown crystal |
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| Solubility = Insoluble in water, soluble in most organic solvents}} |
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| Density = 1.014 g/mL |
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| Section3 = {{Chembox Hazards |
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| EUIndex = |
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| MeltingPtC = 81 to 83 |
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| MeltingPt_ref = <ref name="sigma">{{Sigma-Aldrich|Aldrich|id=106860|name=Acetylferrocene|accessdate=2013-07-20}}</ref> |
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| EUClass = {{Hazchem T+}} |
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| BoilingPtC = 161 to 163 |
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| RPhrases = {{R24}}, {{R28}} |
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| BoilingPt_notes = (4 mmHg) |
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| SPhrases = {{S1}}, {{S28}}, {{S36/37/39}}, {{S48}}<ref>https://fscimage.fishersci.com/msds/69220.htm</ref> |
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| Solubility = Insoluble in water, soluble in most organic solvents}} |
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| NFPA-H = 4 |
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|Section3={{Chembox Hazards |
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| NFPA-F = 1 |
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| GHSPictograms = {{GHS06}} |
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| NFPA-R = 0 |
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| GHSSignalWord = Danger |
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| LD50 = 25 mg kg<sup>−1</sup> (oral, rat) <br> 50 mg kg<sup>−1</sup> (oral, mouse)<ref>http://msds.chem.ox.ac.uk/AC/acetylferrocene.html</ref> |
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| HPhrases = {{H-phrases|300}} |
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}} |
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| PPhrases = {{P-phrases|264|301+310}} |
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| NFPA-H = 4 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| LD50 = 25 mg kg<sup>−1</sup> (oral, rat)<br/> 50 mg kg<sup>−1</sup> (oral, mouse)<ref>http://msds.chem.ox.ac.uk/AC/acetylferrocene.html {{Dead link|date=August 2022}}</ref> |
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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>COCH<sub>3</sub>). It consists of ] substituted by an ] on one of the ] rings. It is an orange, air-stable solid that is soluble in organic solvents. |
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'''Acetylferrocene''' is an ] compound based on ] with one ] added to the ] ring. It is mainly used in military or space field as an additive in rocket propellant, to promote the burning rate.<ref name="use">{{cite web|url=http://watson-int.com/key-products/product-details/14.html|title=Use of Acetylferrocene|publisher=Watson International Ltd|accessdate=2011-07-20}}</ref> |
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==Preparation and reactions== |
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Acetylferrocene is prepared by ] of ferrocene, usually with ] (Ac<sub>2</sub>O): |
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:Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + Ac<sub>2</sub>O → (C<sub>5</sub>H<sub>5</sub>)Fe(C<sub>5</sub>H<sub>4</sub>Ac) + HOAc |
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The experiment is often conducted in the instructional laboratory to illustrate ] as well as chromatographic separations.<ref>Bozak, R. E. "Acetylation of ferrocene: A chromatography experiment for elementary organic laboratory" J. Chem. Educ., 1966, volume 43, p 73.{{doi|10.1021/ed043p73}}</ref><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> |
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Acetylferrocene can be converted to many derivatives, e.g., reduction to the chiral alcohol (C<sub>5</sub>H<sub>5</sub>)Fe(C<sub>5</sub>H<sub>4</sub>CH(OH)Me) and precursor to ]. 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> |
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==References== |
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==References== |
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