56073-10-0

Basic information

• Product Name: Brodifacoum
• Synonyms: KLERAT;KLERAT(R);FORWARAT;HAVOC;BROBAIT;BRODIFACOUM;3-(3-(4'-bromo-(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-naphthyl)-4-hydroxy-2h-1-benzopyran-2-one;3-(3-(4'-Bromo-(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-napthalenyl)-4-hydroxycoumarin
• CAS NO: 56073-10-0
• Molecular Formula: C31H23BrO3
• Molecular Weight: 523.42
• EINECS: 259-980-5
• Product Categories: INSECTICIDE;Alphabetic;B;BI - BZPesticides&Metabolites;Pesticides;Rodenticides;A-BAlphabetic;Alpha sort;Pesticides&Metabolites
• Mol File: 56073-10-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 228-230°
• Boiling Point: 678.995 °C at 760 mmHg
• Flash Point: 364.443 °C
• Appearance: /
• Density: 1.2940 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: 0-6°C
• PKA: 5.0 (weak acid, est.)
• Water Solubility: 0.24 mg l-1 (20 °C)
• Merck: 13,1363
• BRN: 8171403
• CAS DataBase Reference: Brodifacoum(CAS DataBase Reference)
• NIST Chemistry Reference: Brodifacoum(56073-10-0)
• EPA Substance Registry System: Brodifacoum(56073-10-0)

Safety Data

• Hazard Codes: T+;N,N,T+
• Statements: 27/28-48/24/25-50/53
• Safety Statements: 1/2-36/37-45-60-61
• RIDADR: UN 2811
• WGK Germany: 3
• RTECS: GN4934750
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 56073-10-0(Hazardous Substances Data)

Usage

Description

Brodifacoum is a 4-hydroxycoumarin anticoagulant that acts as a vitamin K antagonist. It was registered as a pesticide in 1979 in the United States although in 2008 it was made a restricted use pesticide by the Environmental Protection Agency. This means it can only be used by certified pesticide applicators; however, the makers of D-Con which contains 0.005% brodifacoum by weight have challenged this and brodifacoum is currently available in D-Con and in various other pesticide products for the eradication of mice and rats although it is also used on larger mammals such as possums. Brodifacoum currently remains available to the general public.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 56073-10-0 differently. You can refer to the following data:
1. Brodifacoum is a highly lethal vitamin K antagonist anticoagulant poison. In recent years, Broadifacoum, has become one of the world's most widely used pesticides.
2. Rodenticide.
3. Brodifacoum is used to control rodents in and around buildings.

Hazard

Poison, anticoagulant.

Environmental Fate

Brodifacoum, like other hydroxycoumarins, interferes with the production of vitamin K–dependent coagulation factors. Vitamin K is a cofactor for the carboxylation of specific glutamic acid groups in coagulation factors II (prothrombin), VII, IX, and X. During this step, vitamin K is oxidized to vitamin K 2,3-epoxide. The regeneration of vitamin K by vitamin K 2,3-epoxide reductase is prevented by brodifacoum. As a result, dysfunctional decarboxy-coagulation factors are produced and coagulation is impaired. Brodifacoum is over 100 times more potent than warfarin on a molar basis in rats.

Metabolic pathway

The fate of brodifacoum in soils and plants has not been studied in detail because the compound is usually applied as a pelleted bait or in a wax block. This limits its dissipation in the environment. Studies in animals have been conducted as part of the assessment of safety and to investigate mode of action.

Degradation

Brodifacoum is a stable compound; no detectable degradation occurs at 50 °C or in direct sunlight over 30 days, though it is liable to some photodecomposition in solution.

Toxicity evaluation

Brodifacoum has a very low solubility in water and typically enters water through erosion where it is then found in the sediment. Brodifacoum concentrations are typically not measurable in water systems.Products that contain brodifacoum as pesticide can remain toxic for a long period of time in the environment. The rate of decay of brodifacoum depends upon the amount of rainfall. As the product that contains brodifacoum degrades over time, the brodifacoum is absorbed into the soil. Soil bacteria degrade brodifacoum over weeks to months although soil type, temperature, and the presence of microorganisms that will degrade brodifacoum all influence the time it takes to degrade.

InChI: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

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 182356-08-7 (S)-3-(4'-Bromo-biphenyl-4-yl)-3,4-dihydro-2H-naphthalen-1-one 
• 182356-07-6 (R)-3-(4'-Bromo-biphenyl-4-yl)-3,4-dihydro-2H-naphthalen-1-one 
• 70942-04-0 1-Bromo-3-(4'-bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalene 
• 56181-82-9 (+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol 
• 182511-14-4 (4R,5S)-1-[(S)-3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyryl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 182511-12-2 (4R,5S)-1-[(E)-3-(4'-Bromo-biphenyl-4-yl)-acryloyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 182356-05-4 (4S,5R)-1-[(R)-3-(4'-Bromo-biphenyl-4-yl)-4-phenyl-butyryl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 182356-04-3 (4S,5R)-1-[(E)-3-(4'-Bromo-biphenyl-4-yl)-acryloyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 190729-08-9 (E)-3-(4'-Bromo-biphenyl-4-yl)-acrylic acid ethyl ester 

Relevant articles and documents

Improved synthesis for the rodenticides, diphenacoum and brodifacoum

An improved synthesis of the 3-[3-(p-substituted phenyl)-1,2,3,4-tetrahydro-1-napththyl]-4-hydroxycoumarins, diphenacoum and brodifacoum, is described. The process is primarily based on the formation of one of the crucial bonds in the carbon backbone using organocopper methodology, and on the coupling of the 4-hydroxycoumarin moiety to the 3-biphenyl tetralin unit under strongly acidic conditions.

Rodenticides

Rodenticidal compositions comprising a rodenticidally effective amount of an isomer of a 3-substituted-4-hydroxycoumarin rodenticide which is capable of existing in more than one stable isomeric form. The isomer, for example, the trans isomer of brodifacoum, is significantly less persistently retained in the tissues of non-rodent mammalian or avian species likely to consume the composition or poisoned rodent carcasses than other isomers of the same 3-substituted-4-hydroxycoumarin. The compositins are substantially free of such other isomers, e.g., the cis isomer of brodifacoum, thereby reducing the risk to non-target species from accidental ingestion.