二茂铁甲酸

二茂铁甲酸
识别
CAS号	1271-42-7
性质
化学式	C11H10FeO2
摩尔质量	230.04 g·mol−1
熔点	194—197 °C（467—470 K）（分解）; 205 °C（478 K）（分解）
pKa	6.78
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

二茂铁甲酸是一种有机化合物，化学式为C₁₁H₁₀FeO₂。

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将正丁基锂在搅拌下滴加至二茂铁的无水乙醚溶液中，发生锂化反应（而C-H酸性更弱的苯无明显反应）；待反应结束后将混合物加入至干冰-乙醚的混合物中搅拌，干冰消失后加入冷水，分离出水相后加6 N盐酸酸化，沉淀出产物二茂铁甲酸，副产物二茂铁二甲酸占30%。它们通过在乙酸中结晶分离提纯。^[3]

二茂铁甲酸具有弱酸性，比苯甲酸弱大约三倍。^[3]它可以和碱反应，生成二茂铁甲酸盐；^[4]草酰氯反应，得到二茂铁甲酰氯。^[5]

[1]
Harold Shechter, John F. Helling. Ferrocenyl and 1,1'-Ferrocenylene Grignard Reagents 1a. The Journal of Organic Chemistry. 1961-04, 26 (4): 1034–1037 [2020-12-24]. ISSN 0022-3263. doi:10.1021/jo01063a013 （英语）.
[2]
Andrei S. Batsanov, Damien Hérault, Judith A. K. Howard, Leonard G. F. Patrick, Michael R. Probert, Andrew Whiting. Synthesis and Structure of Planar Chiral, Bifunctional Aminoboronic Acid Ferrocene Derivatives. Organometallics. 2007-04, 26 (9): 2414–2419 [2020-12-24]. ISSN 0276-7333. doi:10.1021/om070038l （英语）.
[3]
Robert A. Benkeser, Donald Goggin, Gene Schroll. A Route to Monosubstituted Ferrocene Compounds. Journal of the American Chemical Society. 1954-08, 76 (15): 4025–4026 [2020-12-24]. ISSN 0002-7863. doi:10.1021/ja01644a047 （英语）.
[4]
Neto, Alberto Federman; Miller, Joseph; Andrade, Vânia Faria de; Fujimoto, Susana Yumi; Afonso, Márcia Maísa de Freitas; Archanjo, Fernando Costa; Darin, Vítor André; Silva, Márcio Luís Andrade e; Borges, Áurea Donizete Lanchote; Ponte, Gino Del. New Synthesis of Ferrocene Monocarboxylic Acid and Systematic Studies on the Preparation of Related Key-Intermediates. Zeitschrift für anorganische und allgemeine Chemie. 2002, 628 (1): 209–216. ISSN 0044-2313. doi:10.1002/1521-3749(200201)628:1<209::AID-ZAAC209>3.0.CO;2-C （德语）.
[5]
Muhammad Saleem, Haojie Yu, Li Wang, Zain-ul-Abdin, Hamad Khalid, Muhammad Akram, Nasir M. Abbasi, Yongsheng Chen. Study on synthesis of ferrocene-based boronic acid derivatives and their saccharides sensing properties. Journal of Electroanalytical Chemistry. 2016-02, 763: 71–78 [2020-12-24]. doi:10.1016/j.jelechem.2015.12.028. （原始内容存档于2018-06-17）（英语）.

[1] [1]
Harold Shechter, John F. Helling. Ferrocenyl and 1,1'-Ferrocenylene Grignard Reagents 1a. The Journal of Organic Chemistry. 1961-04, 26 (4): 1034–1037 [2020-12-24]. ISSN 0022-3263. doi:10.1021/jo01063a013 （英语）.

[2] [2]
Andrei S. Batsanov, Damien Hérault, Judith A. K. Howard, Leonard G. F. Patrick, Michael R. Probert, Andrew Whiting. Synthesis and Structure of Planar Chiral, Bifunctional Aminoboronic Acid Ferrocene Derivatives. Organometallics. 2007-04, 26 (9): 2414–2419 [2020-12-24]. ISSN 0276-7333. doi:10.1021/om070038l （英语）.

[Robert-3] [3]
Robert A. Benkeser, Donald Goggin, Gene Schroll. A Route to Monosubstituted Ferrocene Compounds. Journal of the American Chemical Society. 1954-08, 76 (15): 4025–4026 [2020-12-24]. ISSN 0002-7863. doi:10.1021/ja01644a047 （英语）.

[4] [4]
Neto, Alberto Federman; Miller, Joseph; Andrade, Vânia Faria de; Fujimoto, Susana Yumi; Afonso, Márcia Maísa de Freitas; Archanjo, Fernando Costa; Darin, Vítor André; Silva, Márcio Luís Andrade e; Borges, Áurea Donizete Lanchote; Ponte, Gino Del. New Synthesis of Ferrocene Monocarboxylic Acid and Systematic Studies on the Preparation of Related Key-Intermediates. Zeitschrift für anorganische und allgemeine Chemie. 2002, 628 (1): 209–216. ISSN 0044-2313. doi:10.1002/1521-3749(200201)628:1<209::AID-ZAAC209>3.0.CO;2-C （德语）.

[5] [5]
Muhammad Saleem, Haojie Yu, Li Wang, Zain-ul-Abdin, Hamad Khalid, Muhammad Akram, Nasir M. Abbasi, Yongsheng Chen. Study on synthesis of ferrocene-based boronic acid derivatives and their saccharides sensing properties. Journal of Electroanalytical Chemistry. 2016-02, 763: 71–78 [2020-12-24]. doi:10.1016/j.jelechem.2015.12.028. （原始内容存档于2018-06-17）（英语）.

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二茂铁甲酸

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合成

性质

参考文献

二茂铁甲酸

识别
CAS号	1271-42-7 ^Y
性质
化学式	C₁₁H₁₀FeO₂
摩尔质量	230.04 g·mol⁻¹
熔点	194—197 °C（467—470 K）（分解）^[1] 205 °C（478 K）（分解）^[2]
pK_a	6.78^[3]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。