Brodifacoum

Brodifacoum

Names
IUPAC name 3-[3-[4-(4-Bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-2-hydroxychromen-4-one
Other names Bromfenacoum
Identifiers
CAS Number	56073-10-0 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL233451 Y
ChemSpider	10444663 Y
ECHA InfoCard	100.054.509
PubChem	41736
RTECS number	GN4934750
UNII	A25P3CP5S7 Y
InChI InChI=1S/C31H23BrO3/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2 Y Key: VEUZZDOCACZPRY-UHFFFAOYSA-N Y InChI=1/C31H23BrO3/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2 Key: VEUZZDOCACZPRY-UHFFFAOYAI
SMILES Brc1ccc(cc1)c2ccc(cc2)C4Cc3ccccc3C(C4)C\5=C(/O)c6ccccc6OC/5=O
Properties
Chemical formula	C31H23BrO3
Molar mass	523.43 g·mol−1
Melting point	228 to 230 °C (442 to 446 °F; 501 to 503 K)
Solubility in water	Insoluble
Pharmacology
Pregnancy category	X - Deadly poison
Routes of administration	Oral; dermal; inhalation (dusts) (for poisoning)
Pharmacokinetics:
Bioavailability	100%
Metabolism	slow, incomplete, hepatic
Biological half-life	Slow; 20—130 days
Excretion	faeces; very slow
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	270 μg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide but is also used to control larger pests such as possum.

Brodifacoum has an especially long half-life in the body, which ranges to several months, requiring prolonged treatment with antidotal vitamin K for both human and pet poisonings.

Brodifacoum is a derivative of the 4-hydroxy-coumarin group. Compound 1 is the starting ester needed to synthesize brodifacoum. To obtain this starting compound a simple Wittig condensation of ethyl chloroacetate with 4’-bromobiphenylcarboxaldehyde was accomplished. Compound 1 was transformed into 2 by consecutive hydrolysis, halogenation to form an acid chloride, and then reacted with the required lithium anion. This was done using KOH and EtOH for hydrolysis, and then adding SOCl₂ for chlorination to form the acid chloride which reacted with the addition of lithium anion. Compound 2 was then transformed using organocopper chemistry to yield compound 3 with good regioselectivity of about 98%. Typically a Friedel-Crafts type cyclization would be utilized to obtain the two ring system portion of compound 4, but there were issues of low yield. Instead trifluoromethanesulfonic acid in dry benzene catalyzed the cyclization in good yield. The ketone was then reduced with sodium borohydride yielding a benzyl alcohol. Condensation with 4-hydroxycoumarin under HCl yielded compound 5, brodifacoum.

Brodifacoum is a 4-hydroxycoumarin anticoagulant, with a similar mode of action to its historical predecessors dicoumarol and warfarin. However, due to very high potency and long duration of action (elimination half-life of 20 – 130 days), it is characterised as a "second generation" or "superwarfarin" anticoagulant.