Bathocuproine

Bathocuproine

Names
Preferred IUPAC name 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline
Other names 2,9-Dimethyl-4,7-diaphenyl-1,10-phenanthroline 2,9-Dimethyl-4,7-diphenylphenanthroline 4,7-Diphenyl-2,9-dimethyl-1,10-phenanthroline BCP
Identifiers
CAS Number	4733-39-5
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL220061
ChemSpider	58658
ECHA InfoCard	100.022.945
EC Number	225-240-5
PubChem CID	65149
UNII	9THP2V94FX
CompTox Dashboard (EPA)	DTXSID4063585
InChI InChI=1S/C26H20N2/c1-17-15-23(19-9-5-3-6-10-19)21-13-14-22-24(20-11-7-4-8-12-20)16-18(2)28-26(22)25(21)27-17/h3-16H,1-2H3 Key: STTGYIUESPWXOW-UHFFFAOYSA-N
SMILES CC1=NC2=C(C=CC3=C2N=C(C=C3C4=CC=CC=C4)C)C(=C1)C5=CC=CC=C5
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
Hazards
GHS labelling:
Pictograms
Signal word	Warning
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

Bathocuproine is an organic compound with the formula (C₆H₅)₂(CH₃)₂C₁₂H₄N₂. It is related to 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

1. 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.
2. 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.
3. 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.
4. Guosheng Liu, Yichen, Wu (2012). "Bathocuproine". Encyclopedia of Reagents for Organic Synthesis. eEROS. doi:10.1002/047084289X.rn01392. ISBN   978-0471936237.