Brodifacoum

Base Information

• Chemical Name: Brodifacoum
• CAS No.: 56073-10-0
• Molecular Formula: C₃₁H₂₃BrO₃
• Molecular Weight: 523.426
• Mol file: 56073-10-0.mol

Synonyms:Talon Rodenticide;BFC;Brodimat;Klerat;Klerat Block;Talon;Talon (rodenticide);Volid;WBA 8119;

Chemical Property of Brodifacoum

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 228-230oC
• Refractive Index: 1.686
• Boiling Point: 678.995 °C at 760 mmHg
• PKA: 5.0 (weak acid, est.)
• Flash Point: 364.443 °C
• PSA: 50.44000
• Density: 1.432 g/cm³
• LogP: 7.79000
• Storage Temp.: 0-6°C
• Water Solubility.: 0.24 mg l-1 (20 °C)

Purity/Quality:

97% ^*data from raw suppliers

Brodifacoum ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N; T+
• Hazard Codes: T+;N,N,T+
• Statements: 27/28-48/24/25-50/53
• Safety Statements: 1/2-36/37-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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.
• Uses: 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. Rodenticide. Brodifacoum is used to control rodents in and around buildings.

Technology Process of Brodifacoum

There total 33 articles about Brodifacoum which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(E)-3-(4'-Bromo-biphenyl-4-yl)-acrylic acid ethyl ester (190729-08-9) → 3S-(4'-bromobiphenyl-4-yl)-1R-(4-hydroxycoumarin-3-yl)-1,2,3,4-tetrahydronaphthalene (56073-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: KOH / H₂O / 6 h / 60 °C

2: SOCl₂ / 12 h / Ambient temperature

3: 70 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 0 deg C, 1 h

4: 1.) CuI, TMEDA, 2.) dibutylborontriflate / 1.) THF, -78 deg C, 15 min, 2.) THF, -30 deg C, 12 h

5: 80 percent / trifluoromethanesulfonic acid / benzene / 80 °C

6: 1.) NaBH₄ / 1.) EtOH-THF (1:1), room temp., 4 h, 2.) 160 deg C, 30 min, under HCl(g) atmosphere

With potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; In tetrahydrofuran; water; benzene;

DOI:10.1016/S0040-4020(97)00254-8

Reference yield:

(E)-3-(4'-Bromo-biphenyl-4-yl)-acrylic acid ethyl ester (190729-08-9) → 3-[(1R,3R)-3-(4'-Bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-4-hydroxy-chromen-2-one (56073-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: KOH / H₂O / 6 h / 60 °C

2: SOCl₂ / 12 h / Ambient temperature

3: 73 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 0 deg C, 1 h

4: 1.) CuI, TMEDA, 2.) dibutylborontriflate / 1.) THF, -78 deg C, 15 min, 2.) THF, -30 deg C, 12 h

5: 79 percent / trifluoromethanesulfonic acid / benzene / 80 °C

6: 1.) NaBH₄ / 1.) EtOH-THF (1:1), room temp., 4 h, 2.) 160 deg C, 30 min, under HCl(g) atmosphere

With potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; In tetrahydrofuran; water; benzene;

DOI:10.1016/S0040-4020(97)00254-8

Reference yield:

(E)-3-(4'-Bromo-biphenyl-4-yl)-acrylic acid ethyl ester (190729-08-9) → 3S-(4'-bromobiphenyl-4-yl)-1S-(4-hydroxycoumarin-3-yl)-1,2,3,4-tetrahydronaphthalene (56073-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: KOH / H₂O / 6 h / 60 °C

2: SOCl₂ / 12 h / Ambient temperature

3: 70 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 0 deg C, 1 h

4: 1.) CuI, TMEDA, 2.) dibutylborontriflate / 1.) THF, -78 deg C, 15 min, 2.) THF, -30 deg C, 12 h

5: 80 percent / trifluoromethanesulfonic acid / benzene / 80 °C

6: 1.) NaBH₄ / 1.) EtOH-THF (1:1), room temp., 4 h, 2.) 160 deg C, 30 min, under HCl(g) atmosphere

With potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; In tetrahydrofuran; water; benzene;

DOI:10.1016/S0040-4020(97)00254-8

upstream raw materials:

4-hydroxy[1]benzopyran-2-one

(+/-)-cis/trans-3-(4''-Bromobiphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol

1-Bromo-3-(4'-bromo-biphenyl-4-yl)-1,2,3,4-tetrahydro-naphthalene

(R)-3-(4'-Bromo-biphenyl-4-yl)-3,4-dihydro-2H-naphthalen-1-one

Refernces

• 1、 Van Heerden, Pieter S.,Bezuidenhoudt, Barend C. B.,Ferreira, Daneel. "Improved synthesis for the rodenticides, diphenacoum and brodifacoum". . p. 1141 - 1146. Retrieved 2007/10/03.