PHENPROCOUMON

Details:

Melting point     179-180°
Boiling point     463.2±45.0 °C(Predicted)
density     1.261±0.06 g/cm3(Predicted)
storage temp.     Sealed in dry,2-8°C
pka    4.50±1.00(Predicted)
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)
MSDS Information
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