2-P-ANISYL-1,3-INDANDIONE Chemical Properties

Melting point:

156-157°

Boiling point:

355.44°C (rough estimate)

Density 

1.1824 (rough estimate)

refractive index 

1.5600 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly)

form 

Solid

pka

pKa 4.13(H2O t=25.0±0.1 I=0.1(NaCl)) (Uncertain)

color 

White to Off-White

EPA Substance Registry System

Anisindione (117-37-3)

Safety Information

RIDADR 

2811

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

117-37-3(Hazardous Substances Data)

Toxicity

mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),Journal of Medicinal Chemistry. Vol. 28, Pg. 1591, 1985.

2-P-ANISYL-1,3-INDANDIONE Usage And Synthesis

Chemical Properties

Slightly beige or yellow powder

Originator

Miradon,Schering,US,1960

Uses

radiopaque agent

Uses

Anisindione is a synthetic anticoagulant that prevents the formation of active procoagulation factors and proteins in the liver.

Definition

ChEBI: A cyclic beta-diketone consisting of indane-1,3-dione having a 4-methoxyphenyl substituent at the 4-position.

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.

brand name

Miradon (Schering).

Therapeutic Function

Anticoagulant

General Description

Anisindione, 2-(p-methoxyphenyl)-1,3-indandione, 2-(p-anisyl)-1,3-indandione (Miradon), is ap-methoxy congener of phenindione. It is a white, crystallinepowder, slightly soluble in water, tasteless, and absorbedwell after oral administration.
In instances when the urine may be alkaline, an orangecolor may be detected. This is caused by metabolic productsof anisindione and is not hematuria.

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.]

2-P-ANISYL-1,3-INDANDIONE(117-37-3)Related Product Information

• Anethole trithione
• Indene
• 1H-Indene-1,3(2H)-dione, 2-hydroxy-2-(2-hydroxy-4,5-dimethoxyphenyl)-
• 1,3-Indandione, 2-(3,4-dimethoxy-2-hydroxyphenyl)-2-hydroxy-
• 2-BENZYL-2-(4-METHOXYPHENYL)-1H-INDENE-1,3(2H)-DIONE
• 2-P-ANISYL-1,3-INDANDIONE
• 1,3-Indandione, 2-hydroxy-2-(2-hydroxy-4,5,6-trimethoxyphenyl)-
• 2-Hydroxy-2-(2-hydroxy-4-methoxyphenyl)-1H-indene-1,3(2H)-dione
• 2-BROMO-2-(4-METHOXYPHENYL)INDANE-1,3-DIONE