117-37-3

Basic information

• Product Name: 2-P-ANISYL-1,3-INDANDIONE
• Synonyms: ANISINDIONE;2-P-ANISYL-1,3-INDANDIONE;1,3-Indandione, 2-(p-methoxyphenyl)-;1H-Indene-1,3(2H)-dione, 2-(4-methoxyphenyl)-;2-(4-Methoxyphenyl)-1H-indene-1,3(2H)-dione;spe2792;unidione;Unidone
• CAS NO: 117-37-3
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.26
• EINECS: 204-186-6
• Product Categories: OPTIRAY;Inhibitors
• Mol File: 117-37-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 156-157°
• Boiling Point: 355.44°C (rough estimate)
• Flash Point: 199.8°C
• Appearance: /
• Density: 1.1824 (rough estimate)
• Vapor Pressure: 4.45E-08mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly)
• PKA: pKa 4.13(H2O t=25.0±0.1 I=0.1(NaCl)) (Uncertain)
• CAS DataBase Reference: 2-P-ANISYL-1,3-INDANDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-P-ANISYL-1,3-INDANDIONE(117-37-3)
• EPA Substance Registry System: 2-P-ANISYL-1,3-INDANDIONE(117-37-3)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 117-37-3(Hazardous Substances Data)

Usage

Description

2-P-ANISYL-1,3-INDANDIONE, also known as Anisindione or Miradon, is a synthetic anticoagulant and a p-methoxy congener of phenindione. It is a white, crystalline powder that is slightly soluble in water, tasteless, and well-absorbed after oral administration. Anisindione is a cyclic beta-diketone consisting of indane-1,3-dione with a 4-methoxyphenyl substituent at the 4-position. It is used in the medical field to prevent the formation of active procoagulation factors and proteins in the liver.

Uses

Used in Pharmaceutical Industry:
2-P-ANISYL-1,3-INDANDIONE is used as an anticoagulant for preventing the formation of active procoagulation factors and proteins in the liver. It helps in managing and treating blood clotting disorders.
Used in Medical Imaging:
2-P-ANISYL-1,3-INDANDIONE is used as a radiopaque agent in medical imaging, particularly in diagnostic procedures that require the visualization of blood vessels and other internal structures. Its radiopaque properties allow for better contrast and imaging results.

Originator

Miradon,Schering,US,1960

Manufacturing Process

To a hot solution of 20.6 g of sodium in 400 ml of absolute ethanol, there is added a solution of 110 g of phthalide and 110 g of p-methoxybenzaldehyde. A vigorous reaction ensues and one-half of the alcohol is distilled off over a two hour period. Ice and water are added to the red solution and the diluted solution is acidified with hydrochloric acid. The resulting gum solidifies and the aqueous phase is removed by decantation. The crude solid is recrystallized twice from two liters of ethanol yielding 2-(p-methoxyphenyl)-1,3-indandione as pale yellow crystals, MP 155-156°C.

Therapeutic Function

Anticoagulant

Purification Methods

Crystallise anisidinone from acetic acid or EtOH. [Horeau & Jacqius Bull Soc Chim Fr 53 1948, Koelsch J Am Chem. Soc 58 1331 1936, Beilstein 8 III 2931.]

InChI:InChI=1/C16H12O3/c1-19-11-8-6-10(7-9-11)14-15(17)12-4-2-3-5-13(12)16(14)18/h2-9,14H,1H3

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 4767-61-7 3-(4-methoxybenzylidene)phthalide 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 7434-84-6 3-(4-methoxybenzylidene)isobenzofuran-1(3H)-one 
• 1807-49-4 2-diazo-indan-1,3-dione 
• 100-66-3 methoxybenzene 
• 131-11-3 phthalic acid dimethyl ester 
• 53917-01-4 1-(4-methoxyphenyl)butan-2-one 
• 20604-08-4 3-amino-2-(4-methoxyphenyl)-1-inden-1-one 
• 93-58-3 benzoic acid methyl ester 
• 5219-04-5 [1-cyano-1-(4-methoxypheny)-methyl] phenyl ketone 
• 104-47-2 p-methoxybenzylnitrile 

Downstream Products

• 92858-68-9 2-Nitro-2-(4-methoxy-phenyl)-indandion-(1,3) 
• 41099-25-6 2,3-bis (4-methoxyphenyl)-1H-inden-1-one 
• 3312-38-7 2-(4-methoxyphenyl)-3-phenyl-1H-inden-1-one 
• 94796-75-5 3-chloro-2-(4-methoxyphenyl)-1-indenone 
• 94796-78-8 3-bromo-2-(4-methoxyphenyl)-1H-inden-1-one 
• 107379-19-1 3-Mercapto-2-(4-methoxy-phenyl)-indene-1-thione 
• 119392-17-5 2-(4-methoxyphenyl)-3-ethylindenone 
• 1217-32-9 2-(4-hydroxyphenyl)-1,3-indandione 
• 7360-89-6 2-(4-anisyl)-2-thiocyanatoindan-1,3-dione 
• 475631-84-6 [2-(4-methoxy-phenyl)-1,3-dioxo-indan-2-yl]-phenyl-acetic acid methyl ester 
• 551929-17-0 (3-methoxy-phenyl)-[2-(4-methoxy-phenyl)-1,3-dioxo-indan-2-yl]-acetic acid methyl ester 
• 551929-13-6 (4-methoxy-phenyl)-[2-(4-methoxy-phenyl)-1,3-dioxo-indan-2-yl]-acetic acid methyl ester 
• 94796-58-4 3-aziridino-2-(4-methoxyphenyl)-1-indenone 
• 551929-12-5 C₂₄H₂₀O 

Relevant articles and documents

Reinvestigation of Atipamezole Synthesis and Preparation of New Analogs

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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.

Synthesis and pharmacological properties of sulfur derivatives of indane-1,3-dione

Synthesis of sulfur derivatives of indane-1,3-dione, VIIb-c, VIIIa-b, IX and X is described. Results of a preliminary pharmacological screening of six compounds [VIIb, VIII, VIIIb, IX, X and XI] are presented.