Warfarin

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Warfarin
Names
IUPAC name
(RS)-4-Hydroxy-3-(3-oxo-1-phenylbutyl)- 2H-chromen-2-one
Other names
4-hydroxy-2-oxo-3-(3-oxo-1-phenyl-butyl)-2H-chromene
4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one
Coumadin
Coumafene
Prothromadin
Properties
C19H16O4
Molar mass 308.333 g/mol
Appearance White solid
Odor Odorless
Density 1.4 g/cm3
Melting point 161 °C (322 °F; 434 K)
Boiling point Decomposes
0.17 g/100 ml (20 °C)
Solubility Soluble in acetone, chloroform, DCM, dioxane
Moderately soluble in ethanol, isopropanol, methanol, some oils
Freely soluble in alkaline aqueous solution (forms a water-sol sodium salt)
Practically insoluble in benzene, cyclohexane, hexane, pentane
Solubility in acetone 6.5 g/100 ml (20 °C)
Solubility in chloroform 5 g/100 ml (20 °C)
Solubility in dioxane 10 g/100 ml (20 °C)
Vapor pressure 0.09 mmHg at 20 °C
Acidity (pKa) 5.87
Hazards
Safety data sheet DuPont
Lethal dose or concentration (LD, LC):
1.6 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Warfarin, sold under the brand name Coumadin among others, is an organic chemical compound, used and sold as anticoagulant (blood thinner) in medicine.

Properties

Chemical

Warfarin consists of a racemic mixture of two active enantiomers—R- and S- forms—each of which is cleared by different pathways. S-warfarin is 2-5 times more potent than the R-isomer in producing an anticoagulant response.

Physical

Warfarin is a colorless solid, odorless and tasteless. It is almost insoluble in water, but more soluble in some organic solvents, like acetone, halogenated solvents (chloroform), dioxane.

Availability

Warfarin is sold in pharmacies, though it can only be acquired via prescription.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

Preparation

Warfarin can be prepared from coumarin, which itself can be obtained from the fermentation of sweet clover, though the amount obtained from this route is very small to be practical. It's better to use synthetic coumarin as precursor.

A much quicker route involves 4-hydroxycoumarin and benzalacetone. The reaction produces racemic warfarin.

Projects

  • Pesticide
  • Compound collecting

Handling

Safety

Warfarin is toxic if ingested and large amounts may lead to death. Vitamin K is used as antidote.

Storage

Warfarin should kept in sealed vials, with a proper hazardous chemical label.

Disposal

Should be destroyed with an oxidizing mixture, like chromic acid, Fenton's reagent or piranha solution.

References

Relevant Sciencemadness threads