1,10-Phenanthroline
Names | |
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Preferred IUPAC name
1,10-Phenanthroline[1] | |
Identifiers | |
3D model (
JSmol ) |
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126461 | |
ChEBI | |
ChEMBL |
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ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.000.572 |
EC Number |
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4040 | |
KEGG | |
PubChem CID
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RTECS number
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UNII |
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UN number | 2811 |
CompTox Dashboard (EPA)
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Properties | |
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)[2] |
Boiling point | 409.2[2] |
high[2] | |
Solubility in other solvents | acetone, ethanol[2] |
Acidity (pKa) | 4.84 (phenH+)[2] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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mild neurotoxin, strong nephrotoxin, and powerful diuretic |
GHS labelling: | |
Danger | |
H301, H410 | |
P264, P270, P273, P301+P310, P321, P330, P391, P405, P501 | |
Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,10-Phenanthroline (phen) is a
Abbreviated "phen", it is used as a
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.
Coordination chemistry
In terms of its coordination properties, phenanthroline is similar to
Several homoleptic complexes are known of the type [M(phen)3]2+. Particularly well studied is [Fe(phen)3]2+, called "
Copper(I) forms [Cu(phen)2]+, which is luminescent.[11][12]
Bioinorganic chemistry
1,10-Phenanthroline is an
Related phen ligands
A variety of substituted derivatives of phen have been examined as ligands.[12][15] Substituents at the 2,9 positions confer protection for the attached metal, inhibiting the binding of multiple equivalents of the phenanthroline. Such bulky ligands also favor trigonal or tetrahedral coordination at the metal.[16] Phen itself form complexes of the type [M(phen)3]Cl2 when treated with metal dihalides (M = Fe, Co, Ni). By contrast, neocuproine and bathocuproine form 1:1 complexes such as [Ni(neocuproine)Cl2]2.[17]
phen derivative | pKa | comment/alt. name | numbering scheme |
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1,10-phenanthroline | 4.86 | phen | |
2,2'-bipyridine |
4.30 | bipy | |
5-nitro-1,10-phenanthroline | 3.57 | ||
2,9-dimethyl-1,10-phenanthroline | unknown | neocuproine[19][20] | |
2,9-Dimethyl-4,7-diphenylphenanthroline | unknown | Bathocuproine[19][21] | |
4,7-dimethyl-1,10-phenanthroline | 5.97 | ||
4,7-diphenyl-1,10-phenanthroline | unknown | bathophenanthroline[22] | |
5,6-dimethyl-1,10-phenanthroline | 5.20 | 5,6-Me2phen | |
3,4,7,8-tetramethylphenanthroline | 6.31 | 3,4,7,8-Me4phen[23] | |
4,7-dimethoxy-1,10-phenanthroline | 6.45 | 4,7-(MeO)2phen[24] | |
2,6-dimesitylphenanthroline | unknown | HETPHEN[25][16] |
As an indicator for alkyllithium reagents
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
See also
- Ferroin – Complex of Fe2+ by ortho-phenanthroline
References
- ISBN 978-0-85404-182-4.
- ^ ISBN 978-1-4987-5429-3.
- ISBN 978-0-08-043748-4.
- .
- PMID 20983293.
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- PMID 20415494.
- ISBN 978-0-470-13239-5.
- S2CID 6483735.
- doi:10.1039/b000703j.
- ^ .
- PMID 13892106.
- ISBN 978-0-19-963662-4.
- PMID 19587962.
- ^ PMID 32520556.
- .
- .
- ^ PMID 28594543.
- ISBN 978-0-471-93623-7.
- ISBN 978-0-471-93623-7.
- ISBN 978-0-471-93623-7.
- ISBN 978-0-471-93623-7.
- ISBN 978-0-471-93623-7.
- PMID 26924711.
- ^ Fagan, Paul J.; Nugent, William A. (1998). "1-Phenyl-2,3,4,5-Tetramethylphosphole". Organic Syntheses; Collected Volumes, vol. 9, p. 653.
- .