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ChemicalBook--->CAS DataBase List--->83-12-5

83-12-5

83-12-5 Structure

83-12-5 Structure
IdentificationMore
[Name]

2-PHENYL-1,3-INDANDIONE
[CAS]

83-12-5
[Synonyms]

2-PHENYL-1,3-DIKETOHYDRINDENE
2-PHENYL-1,3-INDANDIONE
2-PHENYL-1,3-INDANEDIONE
2-PHENYL-1H-INDEN-1,3(2H)-DIONE
AURORA KA-4422
PHENINDIONE
PHENINDONE
PHENYLINDIONE
1,3(2H)-Indenedione, 2-phenyl-
1,3-Indandione, 2-phenyl-
1,3-Indandione,2-phenyl-
1H-Indene-1,3(2H)-dione, 2-phenyl-
1H-Indene-1,3(2H)-dione,2-phenyl-
2-fenyloindandion-1,3
2-Phenyl-1H-indene-1,3(2H)-dione
2-phenyl-1h-indene-3(2h)-dione
2-phenyl-3-indandione
2-Phenyl-indan-1,3-dione
2-Phenylindan-1,3-dione
2-phenylindan-1-3-dione
[EINECS(EC#)]

201-454-4
[Molecular Formula]

C15H10O2
[MDL Number]

MFCD00003782
[Molecular Weight]

222.24
[MOL File]

83-12-5.mol
Chemical PropertiesBack Directory
[Appearance]

light yellow fluffy fine flakes
[Melting point ]

144-148 °C(lit.)
[Boiling point ]

243.3 °C (0.3 mmHg)
[density ]

1.1404 (rough estimate)
[refractive index ]

1.6600 (estimate)
[Fp ]

208 °C
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

Very slightly soluble in water; slightly soluble in ethanol (96%) and in ether. Solutions are yellow to red.
[form ]

powder to crystal
[pka]

pKa 4.09(H2O,t =25,I=0.1) (Uncertain)
[color ]

White to Light yellow
[Merck ]

7234
[CAS DataBase Reference]

83-12-5(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

R25:Toxic if swallowed.
[Safety Statements ]

S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

NK6125000
[HS Code ]

2914.39.9000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[Hazardous Substances Data]

83-12-5(Hazardous Substances Data)
Hazard InformationBack Directory
[Description]

Phenindione is an anticoagulant and vitamin K antagonist. It inhibits the reduction of vitamin K1 epoxide to vitamin K1 by vitamin K1 epoxide reductase in rat liver homogenates in a concentration-dependent manner. In vivo, phenindione (500 mg/kg) inhibits prothrombin synthesis and conversion of vitamin K1 epoxide to vitamin K1 in rats by 50 and 57%, respectively. Dietary administration of phenindione (4 mg/kg per day) inhibits aortic atherosclerosis or intracardial thrombosis in rat models of diet-induced atherosclerosis or intravascular thrombosis, respectively.
[Chemical Properties]

light yellow fluffy fine flakes
[Uses]

Like coumarin derivatives, phenindione, a compound of the indandione class, acts by altering biosynthesis of coagulant proteins in the liver. It is used for preventing and treating thrombosis, thrombophlebitis, and thromboembolism. However, because of a number of side effects such as polyurea, polydipsia, tachycardia, and others, it is rarely used in practical medicine.
[Uses]

Oral anticoagulant (indanedione).
[Definition]

ChEBI: Phenindione is a beta-diketone and an aromatic ketone. It has a role as an anticoagulant. It derives from a hydride of an indane.
[Brand name]

Hedulin (Sanofi Aventis).
[Clinical Use]

Anticoagulant
[Synthesis]

Phenindione, 3-phenylindan-1,3-dion (24.1.16), is synthesized in two ways. The first consists of condensating benzaldehyde with phthalide in the presence of sodium ethoxide. Evidently, the resulting phenylmethylenphthalide (24.1.15) rearranges under the reaction conditions to give the desired phenindione (24.1.16). The second method consists of condensation of phenylacetic acid with phthalic anhydride, forming phenylmethylenphthalide (24.1.15), which rearranges further in the presence of sodium ethoxide to phenindione.

Synthesis_83-12-5

[Drug interactions]

Potentially hazardous interactions with other drugs There are many significant interactions with coumarins. Prescribe with care with regard to the following:
Anticoagulant effect enhanced by: alcohol, amiodarone, anabolic steroids, aspirin, aztreonam, bicalutamide, cephalosporins, chloramphenicol, cimetidine, ciprofloxacin, dronedarone, fibrates, clopidogrel, cranberry juice, danazol, dipyridamole, disulfiram, fibrates, grapefruit juice, levofloxacin, macrolides, metronidazole, nalidixic acid, neomycin, norfloxacin, NSAIDs, ofloxacin, paracetamol, penicillins, ritonavir, rosuvastatin, sulphonamides, thyroid hormones, testosterone, tetracyclines, tigecycline, tramadol, trimethoprim.
Anticoagulant effect decreased by: oral contraceptives, rifamycins, vitamin K.
Anticoagulant effects enhanced/reduced by: anion exchange resins, corticosteroids, dietary changes, enteral feeds.
Analgesics: increased risk of bleeding with IV diclofenac and ketorolac - avoid.
Anticoagulants: increased risk of haemorrhage with apixaban, dabigatran, edoxaban and rivaroxaban - avoid.
Ciclosporin: there have been a few reports of altered anticoagulant effect; decreased ciclosporin levels have been seen rarely
[Metabolism]

Hepatically metabolised. Metabolites of phenindione often colour the urine pink or orange.
[storage]

Store at -20°C
[Purification Methods]

Crystallise the dione from EtOH (m 156o) or CHCl3 (m 148-150o). [Beilstein 7 H 808, 7 III 4100, 7 IV 2570.]
Spectrum DetailBack Directory
[Spectrum Detail]

2-PHENYL-1,3-INDANDIONE(83-12-5)MS
2-PHENYL-1,3-INDANDIONE(83-12-5)1HNMR
2-PHENYL-1,3-INDANDIONE(83-12-5)13CNMR
2-PHENYL-1,3-INDANDIONE(83-12-5)IR1
2-PHENYL-1,3-INDANDIONE(83-12-5)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-Phenyl-1H-inden-1,3(2H)-dione, 99%(83-12-5)
[Sigma Aldrich]

83-12-5(sigmaaldrich)
[TCI AMERICA]

2-Phenyl-1,3-indandione,>97.0%(GC)(83-12-5)
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