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| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 454070258 | verifiedrevid = 454070258
| ImageFile = Acetylferrocene.gif | ImageFile1 = Acetylferrocene.svg
| ImageSize = 150px | ImageSize1 = 150px
| ImageFile2 = Crystals of acetylferrocene.jpg
⚫ | ImageAlt = Acetylferrocene
| IUPACName = | ImageSize2 = 150px
⚫ | ImageAlt = Acetylferrocene
| IUPACName = Acetylferrocene
| OtherNames = Acetylferrocene | OtherNames = Acetylferrocene
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1271-55-2 | CASNo = 1271-55-2
| ChemSpiderID = 21241939
⚫ | PubChem =
| SMILES = }} | EINECS = 215-043-2
⚫ | PubChem = 10857189
⚫ | Section2 = {{Chembox Properties
| RTECS = OB3700000
| Formula =
| 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;
⚫ | MolarMass = 228.07 g/mol
| InChIKey = PHMAOJNZIFULOG-UHFFFAOYSA-N
⚫ | Appearance = Red brown crystal
| SMILES = CC(=O)11.11.
| Density =
}}
⚫ | MeltingPt = 81-83 °C<ref name="sigma">{{Sigma-Aldrich|Aldrich|id=106860|name=Acetylferrocene|accessdate=2013-07-20}}</ref>
⚫ |Section2={{Chembox Properties
| BoilingPt = 161-163 °C (4 mmHg)
| Formula =
⚫ | Solubility = Insoluble in water, soluble in most organic solvents}}
⚫ | MolarMass = 228.07 g/mol
⚫ | Section3 = {{Chembox Hazards
⚫ | Appearance = Red brown crystal
| EUIndex =
| EUClass = {{Hazchem T+}} | Density = 1.014 g/mL
| MeltingPtC = 81 to 83
| RPhrases = {{R24}}, {{R28}}
⚫ | MeltingPt_ref = <ref name="sigma">{{Sigma-Aldrich|Aldrich|id=106860|name=Acetylferrocene|accessdate=2013-07-20}}</ref>
| SPhrases = {{S1}}, {{S28}}, {{S36/37/39}}, {{S48}}<ref>https://fscimage.fishersci.com/msds/69220.htm</ref>
| BoilingPtC = 161 to 163
⚫ | NFPA-H = 4
| BoilingPt_notes = (4 mmHg)
⚫ | NFPA-F = 1
⚫ | Solubility = Insoluble in water, soluble in most organic solvents}}
⚫ | NFPA-R = 0
⚫ |Section3={{Chembox Hazards
⚫ | 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>
| GHSPictograms = {{GHS06}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|300}}
| PPhrases = {{P-phrases|264|301+310}}
⚫ | NFPA-H = 4
⚫ | NFPA-F = 1
⚫ | NFPA-R = 0
⚫ | 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>
}} }}
}} }}


'''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.
]


==Preparation and reactions==
'''Acetylferrocene''' is an ] compound based on ] with one ] added to one of the ] rings. It was originally used in military or space field as an additive in rocket propellant, to promote the burning rate. But nowadays, ferrocenyl derivative has wide applications to biological and medical fields such as ferrocene-modified beta-lactam because of its physiological activity of anti-malarial, anti-tumor, bactericidal, anti-inflammatory, treatment of anemia, inhibition of enzymatic activity and so on by virtue of its unique structure and diverse properties, Good stability, high toxicity; Aromatic, easy for substitution reaction and modification; Hydrophobic, attacking a variety of enzymes in cells, DNA, RNA by going through cell membrane; Strong selectivity by its thickness of the sandwich structure, which can stop it close to the activity site of enzymes; Redox reversibility, which enable it to involve in metabolism by enzymes. <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 ].
Acetylferrocene is prepared by ] of ferrocene, usually with ] (Ac<sub>2</sub>O):
: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


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>
⚫ == References ==

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>

⚫ ==References==
{{reflist}} {{reflist}}


==External links==
⚫ ]
*{{Commons category-inline}}
⚫ ]

]
⚫ ]
] ]
⚫ ]

Latest revision as of 02:33, 15 November 2024

Acetylferrocene
Names
IUPAC name Acetylferrocene
Other names Acetylferrocene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.676 Edit this at Wikidata
EC Number
  • 215-043-2
PubChem CID
RTECS number
  • OB3700000
InChI
  • 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;Key: PHMAOJNZIFULOG-UHFFFAOYSA-N
SMILES
  • CC(=O)11.11.
Properties
Chemical formula
Molar mass 228.07 g/mol
Appearance Red brown crystal
Density 1.014 g/mL
Melting point 81 to 83 °C (178 to 181 °F; 354 to 356 K)
Boiling point 161 to 163 °C (322 to 325 °F; 434 to 436 K) (4 mmHg)
Solubility in water Insoluble in water, soluble in most organic solvents
Hazards
GHS labelling:
Pictograms GHS06: Toxic
Signal word Danger
Hazard statements H300
Precautionary statements P264, P301+P310
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

Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COCH3). It consists of ferrocene substituted by an 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 Friedel-Crafts acylation of ferrocene, usually with acetic anhydride (Ac2O):

Fe(C5H5)2 + Ac2O → (C5H5)Fe(C5H4Ac) + HOAc

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

Acetylferrocene can be converted to many derivatives, e.g., reduction to the chiral alcohol (C5H5)Fe(C5H4CH(OH)Me) and precursor to vinylferrocene. 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. 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
  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

External links

Categories: