Phenidone
Chemical compound From Wikipedia, the free encyclopedia
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Chemical compound From Wikipedia, the free encyclopedia
Phenidone (1-phenyl-3-pyrazolidinone) is an organic compound that is primarily used as a photographic developer. It has five to ten times the developing power as Metol, capable of achieving the same level of development in both less time and at a lower concentration.[1] It also has low toxicity and unlike some other developers, does not cause dermatitis upon skin contact.[2] As a developer, Phenidone is typically used in conjunction with hydroquinone for black and white photography and performs better at lower pH levels.[3]
Names | |
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Preferred IUPAC name
1-Phenylpyrazolidin-3-one | |
Identifiers | |
3D model (JSmol) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.960 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C9H10N2O | |
Molar mass | 162.192 g·mol−1 |
Appearance | Crystal leaflets or needles |
Melting point | 121 °C (250 °F; 394 K) |
10 g/100 ml at 100 °C | |
Solubility in ethanol | 10 g/100 ml (hot) |
Solubility in diethyl ether | practically insoluble |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
Harmful if swallowed |
GHS labelling: | |
Warning | |
H302, H411 | |
P264, P270, P273, P301+P312, P330, P391, P501 | |
Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenidone is Ilford's trademark for this material, which was first filed on Feb. 24, 1953, but has since expired.[4] Although the compound was first prepared in 1890; it was not until 1940 that J. D. Kendall, in the laboratories of Ilford Limited, discovered the reducing properties of this compound. Large scale production did not become feasible until 1951.[5]
Phenidone functions as a reducing agent. It converts to the N-phenyl-hydroxypyrazole. It is oxidized in acidic conditions, contributing the electrons it loses to reduce silver halides such as those found in film:[6]
Phenidone is also a dual cyclooxygenase/lipoxygenase inhibitor, capable of blocking the synthesis of arachidonic acid, which plays a role in causing inflammation in systemic inflammatory response syndrome[7] and neuronal damage in kainic acid-induced seizures.[8]
Phenidone can be prepared by heating phenyl hydrazine with 3-chloropropanoic acid.[2]
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