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

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

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

• 87-41-2 2-benzofuran-1(3H)-one 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 100-52-7 benzaldehyde 
• 24063-03-4 3-amino-2-phenyl-1-indenethione 
• 151-88-2 2-(hydroxymethyl)-2-phenyl-1H-indene-1,3(2H)-dione 
• 53241-62-6 3-(N,N-dimethylamino)-2-phenylindene-1-thione 
• 1807-49-4 2-diazo-indan-1,3-dione 
• 71-43-2 benzene 
• 575-61-1 Isoaurone 
• 170805-72-8 1-(1,3-benzodioxol-5-yl)-1H-pyrrol-2,5-dione 
• 1150-59-0 2-hydroxy-3-phenyl-1,4-naphthoquinone 
• 4995-90-8 1-imino-2-phenyl-1H-indene-3-amine 
• 91-94-1 3,3'-dichlorobenzidine 

Downstream Products

• 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 
• 25098-00-4 3-benzoyloxy-2-phenyl-inden-1-one 
• 94802-89-8 2-allyl-2-phenylindene-1,3(2H)-dione 
• 14303-28-7 3-anilino-2-phenyl-1H-inden-1-one 
• 1801-21-4 2,2'-diphenyl-[2,2']biindenyl-1,3,1',3'-tetraone 
• 38039-65-5 2-(3-Methyl-2-nitro-but-2-enyl)-2-phenyl-indan-1,3-dione 
• 23922-85-2 2-Phenyl-2-(β-acetyl-ethenyl)-indandion-(1.3) 
• 76059-13-7 3-<2-(1,3-Dioxo-2-phenylindanyl)>glutarimid 
• 75243-96-8 (S)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(3-oxo-2-phenyl-3H-inden-1-yl) ester 
• 97760-19-5 2-phenyl-2(4-phtalimidobutyl)indan-1,3-dione 
• 75243-98-0 (S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid 3-oxo-2-phenyl-3H-inden-1-yl ester 
• 75243-91-3 (S)-2,6-Bis-benzyloxycarbonylamino-hexanoic acid 3-oxo-2-phenyl-3H-inden-1-yl ester 
• 87005-25-2 3-trimethylsilyl-3-(2-phenyl-1,3-dioxo-2-indanyl)-2-propenal 

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

Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones

A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library.

Third-Generation Light-Driven Symmetric Molecular Motors

Symmetric molecular motors based on two overcrowded alkenes with a notable absence of a stereogenic center show potential to function as novel mechanical systems in the development of more advanced nanomachines offering controlled motion over surfaces. Elucidation of the key parameters and limitations of these third-generation motors is essential for the design of optimized molecular machines based on light-driven rotary motion. Herein we demonstrate the thermal and photochemical rotational behavior of a series of third-generation light-driven molecular motors. The steric hindrance of the core unit exerted upon the rotors proved pivotal in controlling the speed of rotation, where a smaller size results in lower barriers. The presence of a pseudo-asymmetric carbon center provides the motor with unidirectionality. Tuning of the steric effects of the substituents at the bridgehead allows for the precise control of the direction of disrotary motion, illustrated by the design of two motors which show opposite rotation with respect to a methyl substituent. A third-generation molecular motor with the potential to be the fastest based on overcrowded alkenes to date was used to visualize the equal rate of rotation of both its rotor units. The autonomous rotational behavior perfectly followed the predicted model, setting the stage for more advanced motors for functional dynamic systems.

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.

Design and synthesis of 4-benzyl-1-(2H)-phthalazinone derivatives as novel androgen receptor antagonists

The androgen receptor (AR) plays important roles in multiple physiological functions, including differentiation, growth, and maintenance of male reproductive organs, and also has effects on hair and skin. In this paper, we report the synthesis of nonsteroidal AR antagonists having a 4-benzyl-1-(2H)-phthalazinone skeleton. Among the synthesized compounds, 11c with two ortho-substituents on the phenyl group potently inhibited SC-3 cell proliferation (IC50: 0.18 μM) and showed high wt AR-binding affinity (IC50: 10.9 μM), comparable to that of hydroxyflutamide (3). Compound 11c also inhibited proliferation of LNCaP cells containing T877A-mutated AR. Docking study of 11c with the AR ligand-binding domain indicated that the benzyl group is important for the antagonism. These phthalazinone derivatives may be useful for investigating potential clinical applications of AR antagonists.

Palladium-catalyzed chemoselective synthesis of indane-1,3-dione derivatives via tert-butyl isocyanide insertion

A simple and efficient strategy for the synthesis of indane-1,3-dione derivatives through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. In addition, by applying this protocol as the key step, indenopyrazole derivatives can be easily synthesized in high yields in a one-pot procedure. This methodology is tolerant of a wide range of substrates and applicable to library synthesis.

Palladium(ii)-catalyzed synthesis of functionalized indenones via oxidation and cyclization of 2-(2-arylethynylphenyl)acetonitriles

A one-pot two-step synthesis of versatile indenones has been developed. This palladium(ii)-catalyzed transformation involves generation and condensation of ortho-functionalized 1,2-benzils from 2-(2-arylethynylphenyl)acetonitriles using Ph2SO as the oxidant. The resulting 3-cyanoindenones can be converted to various valuable molecules.

Synthesis, characterization, antimicrobial activities and QSAR studies of some 10a-phenylbenzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones

A series of 10a-phenylbenzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones (3) has been synthesized and tested for their antimicrobial activity. The antimicrobial evaluation data indicated that compounds, 3b, 3d, 3k and 3m exhibited very promising antibacterial activity and the compounds 3b and 3k exhibited notable activity, almost comparable to penicillin for Staphylococcus aureus and Bacillus subtilis respectively. The derivatives 3g and 3l exhibited high antifungal activity. Moreover, antibacterial activities were more prolific than antifungal activity. The QSAR studies indicated the importance of topological parameters, Kiers second order molecular index (κα 2) and molecular connectivity index (χ) in describing the antibacterial activity and electronic parameters, the energy of highest occupied molecular orbital (HOMO) and the dipole moment (μ) in describing the antifungal activity.

A novel prodrug strategy for β-dicarbonyl carbon acids: Syntheses and evaluation of the physicochemical characteristics of C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrug derivatives

The C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrugs resulting from derivatization at the reactive α-carbon of β-dicarbonyl carbon acid drugs represent a unique approach for improving their chemical stability and aqueous solubility. This work evaluates the physicochemical and in vitro enzymatic bioconversion lability of selected prodrugs of phenylbutazone and phenindione. The POM and POMOM prodrug derivatives of phenylbutazone are highly water soluble (≥250 mg/mL), chemically stable with projected shelf-lives of 4.5 years (pH 3.5, 258C) and 1.1 years (pH 6.0, 25°C), respectively. Interestingly, both prodrug derivatives do not display a pH-dependency typical of many phosphate monoesters, although the similarities of their apparent thermodynamic activation parameters indicate a hydrolysis mechanism similar to other phosphates. These prodrugs undergo alkaline phosphatases catalyzed bioconversion to their respective carbon acids with an expected faster rate exhibited by the POMOM derivatives. Additionally, in marked contrast to the oxidative instability of phenindione, its POM prodrug is stable. The results from these studies reaffirm the rationale of transiently "masking" the reactive a-carbon/proton bond by covalently incorporating a POM or POMOM promoiety. This prodrug strategy presents a twofold advantage, enhancement of aqueous solubility and prevention of oxidative instability, two intrinsic formulation limitations found for β-dicarbonyl carbon acid drugs.