Bathocuproine

Bathocuproine is a derivative of 1,10-phenanthroline with 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. This compound, first prepared by Case and Brennan in the early 1950s [1][2] is a pale yellow solid that is soluble in polar organic solvents.[3]

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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.022.945
EC Number
  • 225-240-5
UNII
  • 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
  • CC1=NC2=C(C=CC3=C2N=C(C=C3C4=CC=CC=C4)C)C(=C1)C5=CC=CC=C5
Properties
C26H20N2
Molar mass 360.460 g·mol−1
Appearance Pale yellow solid
Melting point 283 °C (541 °F; 556 K)
organic solvents
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H413
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

References
  1. 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.
  2. 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.
  3. Guosheng Liu, Yichen, Wu (2012). "Bathocuproine". Encyclopedia of Reagents for Organic Synthesis. eEROS. doi:10.1002/047084289X.rn01392. ISBN 978-0471936237.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
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