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乙酰二茂铁

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乙酰二茂铁
英文名 Acetylferrocene
识别
CAS号 1271-55-2  ✓
PubChem 10857189
SMILES
InChI
InChIKey PHMAOJNZIFULOG-UHFFFAOYSA-N
RTECS OB3700000
性质
化学式 [Fe(C5H4COCH3)(C5H5)]
摩尔质量 228.07 g·mol⁻¹
外观 红棕色晶体
密度 1.014 g/mL
熔点 81-83 °C(354-356 K)([1]
沸点 161-163 °C(434-436 K)(4 mmHg)
溶解性 不溶
溶解性 可溶于有机溶剂
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》(简称“GHS”)中有毒物质的标签图案
GHS提示词 Danger
H-术语 H300
P-术语 P264, P301+310
NFPA 704
NFPA 704.svg
1
4
0
 
致死量或浓度:
LD50中位剂量
25 mg kg−1(大鼠口服)
50 mg kg−1(小鼠口服)[2]
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

乙酰二茂铁是一种有机铁化合物,化学式 (C5H5)Fe(C5H4COMe)。它是二茂铁的衍生物,由其中一个茂环的氢原子被乙酰基取代而成。它是一种对空气稳定的橙色固体,可溶于有机溶剂。

制备和反应

乙酰二茂铁可以由二茂铁和乙酸酐傅-克酰基化反应而成:

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

这个反应通常在教学实验室进行,以说明酰化反应以及色谱分离。[3][4]

乙酰二茂铁可以用来制备衍生物,例如乙醇基二茂铁 (C5H5)Fe(C5H4CH(OH)Me) 和乙烯基二茂铁。对应的氧化产物——乙酰二茂铁(III)阳离子在实验室中用作单电子氧化剂。[5]

参考资料

  1. ^ 来源:Sigma-Aldrich Co., Acetylferrocene (2013-07-20查阅).
  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
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乙酰二茂铁
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