Bathocuproine
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Preferred IUPAC name 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline | |
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ECHA InfoCard | 100.022.945 ![]() |
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Properties | |
Chemical formula | C26H20N2 |
Molar mass | 360.460 g·mol−1 |
Appearance | Pale yellow solid |
Melting point | 283 °C (541 °F; 556 K) |
Solubility in water | organic solvents |
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Hazard statements | H302, H413 |
Precautionary statements | P264, P270, P273, P301+P312, P330, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Bathocuproine is an organic compound with the formula (C6H5)2(CH3)2C12H4N2. It is related to [Phenanthroline|1,10-phenanthroline]] by the placement of two methyl groups and two phenyl groups in the 2,9 and 4,7 positions, respectively. Like 1,10-phenanthroline, bathocuproine is a bidentate chelating ligand. The two methyl groups flank the nitrogen centers, such that bathocuproine is a bulky ligand. It forms a monomeric 1:1 complex with nickel(II) chloride, whereas the less bulky parent phenanthroline forms a 2:1 complex.[1]
This compound was first prepared by Case and Brennan in the early 1950s [2][3] is a pale yellow solid that is soluble in polar organic solvents.[4]
References
- ^ Powers, David C.; Anderson, Bryce L.; Nocera, Daniel G. (2013). "Two-Electron HCl to H2 Photocycle Promoted by Ni(II) Polypyridyl Halide Complexes". Journal of the American Chemical Society. 135 (50): 18876–18883. doi:10.1021/ja408787k. PMID 24245545.
- ^ Case, Francis H.; Brennan, James A. (June 1954). "Substituted 1,10-Phenanthrolines. VII. Synthesis of Certain Phenanthrolines for Use in the Detection of Cu(I) 1". The Journal of Organic Chemistry. 19 (6): 919–922. doi:10.1021/jo01371a007.
- ^ Diehl, Harvey; Smith, George Frederick (1972). The Copper Reagents: Cuproine, Neocuproine, Bathocuproine (PDF) (2nd ed.). Columbus, Ohio: G. Frederick Smith Chemical Company. p. 26. Retrieved 1 January 2023.
- ^ Guosheng Liu, Yichen, Wu (2012). "Bathocuproine". Encyclopedia of Reagents for Organic Synthesis. eEROS. doi:10.1002/047084289X.rn01392. ISBN 978-0471936237.
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