Phenindione

Base Information

• Chemical Name: Phenindione
• CAS No.: 83-12-5
• Molecular Formula: C15H10 O2
• Molecular Weight: 222.243
• Hs Code.: 2914399090
• European Community (EC) Number: 201-454-4
• NSC Number: 757269,41693
• UNII: 5M7Y6274ZE
• DSSTox Substance ID: DTXSID5023453
• Nikkaji Number: J166.097G
• Wikipedia: Phenindione
• Wikidata: Q1640947
• NCI Thesaurus Code: C66371
• Pharos Ligand ID: YZXR726WDAK8
• Metabolomics Workbench ID: 42842
• ChEMBL ID: CHEMBL711
• Mol file: 83-12-5.mol

Synonyms:2 Phenyl 1,3 indandione;2-Phenyl-1,3-indandione;Dindevan;Fenilin;Phenindione;Phenylindanedione;Phenyline;Pindione

Chemical Property of Phenindione

Chemical Property:

• Appearance/Colour: light yellow fluffy fine flakes
• Vapor Pressure: 1.43E-07mmHg at 25°C
• Melting Point: 144-148 °C(lit.)
• Refractive Index: 1.6600 (estimate)
• Boiling Point: 243.3 °C (0.3 mmHg)
• PKA: pKa 4.09(H2O,t =25,I=0.1) (Uncertain)
• Flash Point: 208
• PSA: 34.14000
• Density: 1.343g/cm³
• LogP: 2.84940
• Storage Temp.: 2-8°C
• Solubility.: Very slightly soluble in water; slightly soluble in ethanol (96%) and in ether. Solutions are yellow to red.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 222.068079557
• Heavy Atom Count: 17
• Complexity: 304

Purity/Quality:

99% ^*data from raw suppliers

MTA2 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(=O)C3=CC=CC=C3C2=O
• Recent ClinicalTrials: Start or STop Anticoagulants Randomised Trial (SoSTART)
• Recent EU Clinical Trials: Start or STop Anticoagulants Randomised Trial (SoSTART) after spontaneous intracranial haemorrhage
• 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.
• Uses: Oral anticoagulant (indanedione). 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.
• 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

Technology Process of Phenindione

There total 66 articles about Phenindione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-diazo-3-hydroxy-3-phenyl-1-indanone (79963-47-6) → phenindione (83-12-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; Ambient temperature;

DOI:10.1246/bcsj.54.2142

Reference yield: 97.4%

2-(2-phenylacetyl)benzonitrile (898783-78-3) → phenindione (83-12-5)

Guidance literature:

With dichlorobis(pyridine)palladium(II); 1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane; silver trifluoroacetate; tert-butyl XPhos; In N,N-dimethyl acetamide; at 20 - 85 ℃; for 7h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield: 95.0%

2-diazo-indan-1,3-dione (1807-49-4) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → phenindione (83-12-5)

Guidance literature:

With rhodium(II) acetate; at 50 ℃; for 49h;

DOI:10.1021/jo00247a007

upstream raw materials:

ethylmagnesium iodide

diethyl ether

2-bromo-2-phenyl-indan-1,3-dione

2-benzofuran-1(3H)-one

Downstream raw materials:

3-methoxy-2-phenyl-2-inden-1-one

2-(1-[2]furyl-2-nitro-ethyl)-2-phenyl-indan-1,3-dione

2-allyl-2-phenylindene-1,3(2H)-dione

2,2'-diphenyl-[2,2']biindenyl-1,3,1',3'-tetraone

Refernces

• 1、 Hallur, Gurulingappa,Suresh, Palaniswamy,Tamizharasan, Natarajan. "Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones". . p. 12318 - 12325. Retrieved 2021/09/07.
• 2、 Kistemaker, Jos C. M.,?tacko, Peter,Roke, Diederik,Wolters, Alexander T.,Heideman, G. Henrieke,Chang, Mu-Chieh,Van Der Meulen, Pieter,Visser, Johan,Otten, Edwin,Feringa, Ben L.. "Third-Generation Light-Driven Symmetric Molecular Motors". supporting information. p. 9650 - 9661. Retrieved 2017/07/24.