1,10-Phenanthroline

Phenanthroline
Names
	Preferred IUPAC name 1,10-Phenanthroline
Identifiers
CAS Number	66-71-7 ; monohydrate: 5144-89-8 (monohydrate) ;
3D model (JSmol)	Interactive image; monohydrate: Interactive image;
Beilstein Reference	126461
ChEBI	CHEBI:44975 ;
ChEMBL	ChEMBL415879 ; monohydrate: ChEMBL1255788;
ChemSpider	1278 ; monohydrate: 19955;
DrugBank	DB02365 ;
ECHA InfoCard	100.000.572
EC Number	200-629-2; monohydrate: 627-114-9;
Gmelin Reference	4040
KEGG	C00604;
PubChem CID	1318; monohydrate: 21226;
RTECS number	SF8300000;
UNII	W4X6ZO7939 ; monohydrate: KSX215X00E ;
UN number	2811
CompTox Dashboard (EPA)	DTXSID1025857 ;
	InChI InChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H Key: DGEZNRSVGBDHLK-UHFFFAOYSA-N ; InChI=1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H Key: DGEZNRSVGBDHLK-UHFFFAOYAW;
	SMILES c1cc2ccc3cccnc3c2nc1; monohydrate: C1=CC2=C(C3=C(C=CC=N3)C=C2)N=C1.O;
Properties
Chemical formula	C12H8N2
Molar mass	180.21 g/mol
Appearance	colourless crystals
Density	1.31 g/cm3
Melting point	118.56 °C (245.41 °F; 391.71 K)
Boiling point	409.2
Solubility in water	high
Solubility in other solvents	acetone, ethanol
Acidity (pKa)	4.84 (phenH )
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	mild neurotoxin, strong nephrotoxin, and powerful diuretic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H410
Precautionary statements	P264, P270, P273, P301 P310, P321, P330, P391, P405, P501
Related compounds
Related compounds	2,2'-bipyridine; ferroin; phenanthrene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

1,10-Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. The 1,10 refer to the location of the nitrogen atoms that replace CH's in the hydrocarbon called phenanthrene.

Abbreviated "phen", it is used as a ligand in coordination chemistry, forming strong complexes with most metal ions.^[3]^[4] It is often sold as the monohydrate.

Synthesis

Phenanthroline may be prepared by two successive Skraup reactions of glycerol with o-phenylenediamine, catalyzed by sulfuric acid, and an oxidizing agent, traditionally aqueous arsenic acid or nitrobenzene.^[5] Dehydration of glycerol gives acrolein which condenses with the amine followed by a cyclization.

Reactions

Oxidation of 1,10-phenanthroline with a mixture of nitric and sulfuric acids gives 1,10-phenanthroline-5,6-dione.^[6]

1,10-Phenanthroline forms many coordination complexes. One example is the iron complex called ferroin.

Alkyllithium reagents form deeply colored derivatives with phenanthroline. The alkyllithium content of solutions can be determined by treatment of such reagents with small amounts of phenanthroline (ca. 1 mg) followed by titration with alcohols to a colourless endpoint.^[7] Grignard reagents may be similarly titrated.^[8]

Pharmacology

Phenanthroline is used in scientific research as an inhibitor of the deubiquitination enzyme Rpn11.^[9]

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 211. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b ^c ^d ^e Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.444. ISBN 978-1-4987-5429-3.
^ Luman, C.R. and Castellano, F.N. (2003) "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II. Elsevier. ISBN 978-0-08-043748-4.
^ Sammes, Peter G.; Yahioglu, Gokhan (1994). "1,10-Phenanthroline: A versatile ligand". Chemical Society Reviews. 23 (5): 327. doi:10.1039/cs9942300327.
^ Halcrow, Barbara E.; Kermack, William O. (1946). "43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3′ : 2′-pyridoquinoline)". J. Chem. Soc.: 155–157. doi:10.1039/jr9460000155. PMID 20983293.′ : 2′-pyridoquinoline)&rft.pages=155-157&rft.date=1946&rft_id=info:doi/10.1039/jr9460000155&rft_id=info:pmid/20983293&rft.aulast=Halcrow&rft.aufirst=Barbara E.&rft.au=Kermack, William O.&rfr_id=info:sid/en.wikipedia.org:1,10-Phenanthroline" class="Z3988">
^ Dickeson, JE; Summers, LA (1970). "Derivatives of 1,10-Phenanthroline-5,6-quinone". Australian Journal of Chemistry. 23 (5): 1023. doi:10.1071/ch9701023.
^ Fagan, Paul J.; Nugent, William A. (1998). "1-Phenyl-2,3,4,5-Tetramethylphosphole". Organic Syntheses; Collected Volumes, vol. 9, p. 653.
^ Lin, Ho-Shen; Paquette, Leo A. (1994). "A Convenient Method for Determining the Concentration of Grignard Reagents". Synth. Commun. 24 (17): 2503–2506. doi:10.1080/00397919408010560.2503-2506&rft.date=1994&rft_id=info:doi/10.1080/00397919408010560&rft.au=Lin, Ho-Shen&rft.au=Paquette, Leo A.&rfr_id=info:sid/en.wikipedia.org:1,10-Phenanthroline" class="Z3988">
^ Song, Y.; Li, S.; Ray, A.; Das, D. S.; Qi, J.; Samur, M. K.; Tai, Y.-T.; Munshi, N.; Carrasco, R. D.; Chauhan, D.; Anderson, K. C. (2017-06-05). "Blockade of deubiquitylating enzyme Rpn11 triggers apoptosis in multiple myeloma cells and overcomes bortezomib resistance". Oncogene. 36 (40): 5631. doi:10.1038/onc.2017.172. PMC 5705032. PMID 28581522. Retrieved 2024-12-13.

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 211. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[crc-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.444. ISBN 978-1-4987-5429-3.

[Castellano-3] Luman, C.R. and Castellano, F.N. (2003) "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II. Elsevier. ISBN 978-0-08-043748-4.

[4] Sammes, Peter G.; Yahioglu, Gokhan (1994). "1,10-Phenanthroline: A versatile ligand". Chemical Society Reviews. 23 (5): 327. doi:10.1039/cs9942300327.

[5] Halcrow, Barbara E.; Kermack, William O. (1946). "43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3′ : 2′-pyridoquinoline)". J. Chem. Soc.: 155–157. doi:10.1039/jr9460000155. PMID 20983293.′ : 2′-pyridoquinoline)&rft.pages=155-157&rft.date=1946&rft_id=info:doi/10.1039/jr9460000155&rft_id=info:pmid/20983293&rft.aulast=Halcrow&rft.aufirst=Barbara E.&rft.au=Kermack, William O.&rfr_id=info:sid/en.wikipedia.org:1,10-Phenanthroline" class="Z3988">

[AJC-6] Dickeson, JE; Summers, LA (1970). "Derivatives of 1,10-Phenanthroline-5,6-quinone". Australian Journal of Chemistry. 23 (5): 1023. doi:10.1071/ch9701023.

[7] Fagan, Paul J.; Nugent, William A. (1998). "1-Phenyl-2,3,4,5-Tetramethylphosphole". Organic Syntheses; Collected Volumes, vol. 9, p. 653.

[8] Lin, Ho-Shen; Paquette, Leo A. (1994). "A Convenient Method for Determining the Concentration of Grignard Reagents". Synth. Commun. 24 (17): 2503–2506. doi:10.1080/00397919408010560.2503-2506&rft.date=1994&rft_id=info:doi/10.1080/00397919408010560&rft.au=Lin, Ho-Shen&rft.au=Paquette, Leo A.&rfr_id=info:sid/en.wikipedia.org:1,10-Phenanthroline" class="Z3988">

[i715-9] Song, Y.; Li, S.; Ray, A.; Das, D. S.; Qi, J.; Samur, M. K.; Tai, Y.-T.; Munshi, N.; Carrasco, R. D.; Chauhan, D.; Anderson, K. C. (2017-06-05). "Blockade of deubiquitylating enzyme Rpn11 triggers apoptosis in multiple myeloma cells and overcomes bortezomib resistance". Oncogene. 36 (40): 5631. doi:10.1038/onc.2017.172. PMC 5705032. PMID 28581522. Retrieved 2024-12-13.

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