Phenidone

Last updated
Phenidone
Phenidone.svg
Phenidone-spaceFill.png
Names
Preferred IUPAC name
1-Phenylpyrazolidin-3-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.960 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-155-1
PubChem CID
UNII
  • InChI=1S/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12) Yes check.svgY
    Key: CMCWWLVWPDLCRM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12)
    Key: CMCWWLVWPDLCRM-UHFFFAOYAF
  • O=C2NN(c1ccccc1)CC2
Properties
C9H10N2O
Molar mass 162.192 g·mol−1
AppearanceCrystal 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:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. It also has low toxicity and unlike some other developers, does not cause dermatitis upon skin contact. [1]

Phenidone is Ilford's trademark for this material, which 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. [2]

Phenidone functions as a reducing agent. It converts to the N-phenyl-hydroxypyrazole:

Reaction of phenidone with silver bromide, as occurs in photographic development PhenidoneAction.png
Reaction of phenidone with silver bromide, as occurs in photographic development

Preparation

Phenidone can be prepared by heating phenyl hydrazine with 3-chloropropanoic acid. [1]

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References

  1. 1 2 Merck Index of Chemicals and Drugs, 9th ed. monograph 7115
  2. Karlheinz Keller et al. "Photography" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a20_001