PHENPROCOUMON Chemical Properties

Melting point:

179-180°

Boiling point:

463.2±45.0 °C(Predicted)

Density 

1.261±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.50±1.00(Predicted)

color 

White to Off-White

EPA Substance Registry System

Phenprocoumon (435-97-2)

Safety Information

RIDADR 

2811

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

435-97-2(Hazardous Substances Data)

PHENPROCOUMON Usage And Synthesis

Chemical Properties

White Solid

Originator

Liquamar ,Organon ,US,1958

Uses

Phenprocoumon is known for being an oral anti-coagulant.

Definition

ChEBI: A hydroxycoumarin that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenylpropyl group.

Manufacturing Process

8.3 parts by weight of powdered sodium in 300 parts by volume of benzene, 100 parts by weight of diethyl (1'-phenylpropyl)-malonate and 72 parts by weight of acetylsalicylic acid chloride are reacted together to form diethyl 1(o-acetoxybenzoy1)-1-(1'-phenylpropyl)malonate, which boils at 195°198°C/0.03 mm Hg.
10.3 parts of weight of diethyl 1-(o-acetoxybenzoyl)-1-(1'-phenylpropyl)malonate are dissolved in 60 parts by volume of absolute ether and to this solution are added portion. wise at 10°C, while stirring, 2.6 parts by weight of sodium methylate. The reaction mixture is stirred for 4 hours, whereupon it is poured into ice water. The ether solution is washed neutral with ice water. After having distilled off the ether, a thick oil consisting of 3-carbethoxy-3-(1'phenylpropyl)-4-oxo-dihydrocoumarinis obtained. This compound crystallized in butyl oxide and has a MP of 108°-109°C.
The 3-carbethoxy-3-(1'-phenylpropyl)-4-oxo-dihydrocoumarinmay be hydrolyzed and decarboxylated as follows. The crude product is heated to 85°C for 1/2 hour with 100 parts by volume of 5% aqueous sodium hydroxide, while agitating or stirring. To remove traces of undissolved oil, the cooled solution is treated with 1 part by weight of charcoal, whereupon it is filtrated and acidified to Congo reaction with dilute sulfuric acid. The 3-(1'phenylpropyl)-4-hydroxycoumarin formed is separated off and recrystallized in 80% ethanol, whereupon it melts at 178°-179°C according to US Patent 2,701,804.

brand name

Liquamar (Organon).

Therapeutic Function

Anticoagulant

Synthesis

Phenprocoumon, 3-(|á-ethylbenzyl)-4-hydroxycoumarin (24.1.14), is synthesized by acylating sodium salts of diethyl ester (1-phenylpropyl)butyric acid with acetylsalicylic acid chloride, which forms the compound 24.1.12, which upon reaction with sodium ethoxide cyclizes to 3-(|á-ethylbenzyl)-2-carboethoxy-4-hydroxycoumarin (24.1.13). Alkaline hydrolysis of this product and further decarboxylation gives phenprocoumon(24.1.14).

PHENPROCOUMON(435-97-2)Related Product Information

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• ACENOCOUMAROL
• (S)-(-)-WARFARIN
• 7-HYDROXYWARFARIN
• 10-HYDROXYWARFARIN
• 6-HYDROXYWARFARIN
• 8-HYDROXYWARFARIN
• (R)-(+)-WARFARIN
• 7-HYDROXYWARFARIN
• 4-HYDROXY-3-[1'-(4''-HYDROXYPHENYL)-3'-OXOBUTYL]-2H-1-BENZOPYRAN-2-ONE
• (R)-Phenprocoumon
• Phenprocoumon-d5
• (S)-Phenprocoumon
• phepromaron