83-12-5

Basic information

• Product Name: 2-PHENYL-1,3-INDANDIONE
• Synonyms: AURORA KA-4422;2-PHENYL-1,3-INDANDIONE;2-PHENYL-1,3-INDANEDIONE;2-PHENYL-1,3-DIKETOHYDRINDENE;2-PHENYL-1H-INDEN-1,3(2H)-DIONE;PHENYLINDIONE;PHENINDIONE;PHENINDONE
• CAS NO: 83-12-5
• Molecular Formula: C₁₅H₁₀O₂
• Molecular Weight: 222.24
• EINECS: 201-454-4
• Product Categories: Indane/Indanone and Derivatives;HEDULIN
• Mol File: 83-12-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 144-148 °C(lit.)
• Boiling Point: 243.3 °C (0.3 mmHg)
• Flash Point: 208 °C
• Appearance: /
• Density: 1.1404 (rough estimate)
• Vapor Pressure: 1.43E-07mmHg at 25°C
• Refractive Index: 1.6600 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Very slightly soluble in water; slightly soluble in ethanol (96%) and in ether. Solutions are yellow to red.
• PKA: pKa 4.09(H2O,t =25,I=0.1) (Uncertain)
• Merck: 14,7234
• CAS DataBase Reference: 2-PHENYL-1,3-INDANDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-1,3-INDANDIONE(83-12-5)
• EPA Substance Registry System: 2-PHENYL-1,3-INDANDIONE(83-12-5)

Safety Data

• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NK6125000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 83-12-5(Hazardous Substances Data)

Usage

Description

2-PHENYL-1,3-INDANDIONE, also known as Phenindione, is an indanedione class compound that functions as an anticoagulant and vitamin K antagonist. It inhibits the reduction of vitamin K1 epoxide to vitamin K1 by vitamin K1 epoxide reductase in a concentration-dependent manner, thereby affecting prothrombin synthesis and the conversion of vitamin K1 epoxide to vitamin K1 in vivo.
Used in Pharmaceutical Industry:
2-PHENYL-1,3-INDANDIONE is used as an oral anticoagulant for preventing and treating thrombosis, thrombophlebitis, and thromboembolism. It acts by altering the biosynthesis of coagulant proteins in the liver, similar to coumarin derivatives.
Used in Atherosclerosis and Thrombosis Research:
In rat models of diet-induced atherosclerosis or intravascular thrombosis, dietary administration of 2-PHENYL-1,3-INDANDIONE has been shown to inhibit aortic atherosclerosis or intracardial thrombosis, respectively.
However, due to several side effects such as polyurea, polydipsia, tachycardia, and others, 2-PHENYL-1,3-INDANDIONE is rarely used in practical medicine.

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.

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.

Purification Methods

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

InChI:InChI=1/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,16H

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 60-29-7 diethyl ether 
• 1801-20-3 2-bromo-2-phenyl-indan-1,3-dione 
• 87-41-2 2-benzofuran-1(3H)-one 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 100-52-7 benzaldehyde 
• 103-82-2 phenylacetic acid 
• 85-44-9 phthalic anhydride 
• 29600-47-3 methyl 2-(2-phenylacetyl)benzoate 
• 68306-10-5 1-oxo-2-phenyl-indene-3-carboxylic acid 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 575-61-1 Isoaurone 

Downstream Products

• 2136-67-6 3-methoxy-2-phenyl-2-inden-1-one 
• 112400-94-9 2-(1-[2]furyl-2-nitro-ethyl)-2-phenyl-indan-1,3-dione 
• 10408-73-8 3-methyl-2-phenyl-inden-1-one 
• 102545-95-9 2-(2-nitro-1-phenylethyl)-2-phenyl-1,3-indandione 
• 103388-43-8 2-(2-methyl-1-nitromethyl-propyl)-2-phenyl-indan-1,3-dione 
• 102595-73-3 2-[2-nitro-1-(4-nitro-phenyl)-ethyl]-2-phenyl-indan-1,3-dione 
• 17932-14-8 3-cyclohexyl-2-phenyl-inden-1-one 
• 1947-47-3 3-amino-2-phenyl-1H-inden-1-one 
• 1801-42-9 2,3-diphenyl-1H-inden-1-one 
• 13304-50-2 3-ethyl-2-phenyl-1H-inden-1-one 
• 3817-96-7 2-chloro-2-phenyl-1,3-indandione 
• 1801-20-3 2-bromo-2-phenyl-indan-1,3-dione 
• 1785-91-7 2-nitro-2-phenyl-indan-1,3-dione 
• 1801-21-4 2,2'-diphenyl-[2,2']biindenyl-1,3,1',3'-tetraone 

Relevant articles and documents

Synthesis and properties of macroheterocyclic compounds containing 1-imino-2-phenyl-1H-inden-3-amine fragments

Reaction of 1-imino-2-phenyl-1H-inden-3-amine with 3,3′-dichloro-, 2,2′-disulfo-, and 2,2′-dinitrobiphenyl-4,4′-diamines gave 2: 1 and 1: 2 linear condensation products and symmetrical macroheterocycles. The products were characterized by the IR, UV, and

Reinvestigation of Atipamezole Synthesis and Preparation of New Analogs

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Hydrindene-1,3-dione compound catalysis synthetic method

The present invention relates to a formula (II) shown hydrindene-1,3-dione compound catalysis synthetic method which is as follows: in an organic solvent and under a nitrogen atmosphere, in the presence of a catalyst, an oxidant, and an organic ligand and an adjuvant, self cyclization of a formula (I) compound is performed, the formula (II) compound is obtained by after-treatment after the end of the reaction, the method uses the new catalyst, the oxidant, the organic ligand, the organic solvent and the adjuvant for comprehensive selection and optimization to achieve material high-speed conversion, the yield of the target product can be greatly improved, the needs of industrial production can be better met, and the method has a broad market prospect.