90035-08-8

Basic information

• Product Name: Flocoumafen
• Synonyms: 2h-1-benzopyran-2-one,4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-((4-(trifluoromethy;4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-((4-(trifluoromethyl)phenyl)methoxy)phenyl)-1-naphthalenyl)-2h-1-benzopyran-2-on;4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-(4-trifluoromethylbenzyloxy)phenyl)-1-n;4-hydroxy-3-[1,2,3,4-tetrahydro-3-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1-naphthalenyl]-2H-1-Benzopyran-2-one;aphthyl)coumarin;flocoumafene;l)phenyl)methoxy)phenyl)-1-naphthalenyl)-;stratgem
• CAS NO: 90035-08-8
• Molecular Formula: C33H25F3O4
• Molecular Weight: 542.54
• EINECS: 421-960-0
• Product Categories: Alpha sort;E-GAlphabetic;F;FA - FLPesticides&Metabolites;Pesticides;Pesticides&Metabolites;Rodenticides;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 90035-08-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 181℃ (cis isomer), 163℃ (trans isomer)
• Boiling Point: 640.2°Cat760mmHg
• Flash Point: 23 °C
• Appearance: /
• Density: 1.348g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.629
• PKA: 4.50±1.00(Predicted)
• Water Solubility: 1.1 mg l-1
• CAS DataBase Reference: Flocoumafen(CAS DataBase Reference)
• NIST Chemistry Reference: Flocoumafen(90035-08-8)
• EPA Substance Registry System: Flocoumafen(90035-08-8)

Safety Data

• Hazard Codes: T+,N
• Statements: 26/27/28-48/23/24/25-50/53
• Safety Statements: 28-36/37/39-45-60-61
• RIDADR: 3027
• WGK Germany: 3
• RTECS: DJ3100300
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 90035-08-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 90035-08-8 differently. You can refer to the following data:
1. Flocoumafen is a second-generation anti-coagulant used as a rodenticide. It has a very high toxicity and is restricted to indoor use and sewers (in the United Kingdom). This restriction is mainly due to the increased risk to non-target species. Studies have shown that rodents resistant to first-generation anti-coagulants can be adequately controlled with flocoumafen. The chemical substance is off-white solid, does not mix well with water (1.1 mg/L), and is sparingly soluble in acetone, ethanol, xylene, and octanol. Flocoumafen is stable to hydrolysis. Because of the acute toxicity of flocoumafen and its intended use as a rodenticide, chronic toxicity studies have not been reported. However, flocoumafen is known to cause adverse health effects and abnormal prothrombin.
2. Flocoumafen is used to control rodents around buildings. It also has some use in field and plantation crops including cocoa, cotton, oilpalm, rice and sugar cane.

Metabolic pathway

Flocoumafen exists as cis and trans isomers (Scheme 1). The tetralin ring adopts its most stable conformation in each case and the two forms have very similar shapes. Both are active rodenticides. The fate of flocoumafen in soils and plants has not been studied in detail because the compound is usually used as a pelleted bait or in a wax block. This limits its dissipation in the environment. Studies in animals and birds have been conducted as part of the assessment of safety and to investigate mode of action. Metabolism is slow in the rat and rapid in Japanese quail but this difference should be interpreted with care because of the 100-fold difference in dose used (see also Overview).

Degradation

Flocoumafen is a stable compound; no detectable degradation occurs at 50 °C at pH 7-9 over 4 weeks.

InChI:InChI=1/C33H25F3O4/c34-33(35,36)24-13-9-20(10-14-24)19-39-25-15-11-21(12-16-25)23-17-22-5-1-2-6-26(22)28(18-23)30-31(37)27-7-3-4-8-29(27)40-32(30)38/h1-16,23,28,37H,17-19H2

Upstream product

• 90035-32-8 3-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1(2H)-one 
• 118806-75-0 3-p-methoxyphenyl-2-carboxy-4-phenylbutyric acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 7443-25-6 dimethyl 2-(4-methoxybenzylidene)malonate 
• 61696-79-5 3,4-dihydro-3-(4-methoxyphenyl)naphthalene-1(2H)-one 
• 1333110-92-1 C₂₀H₂₂O₅ 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 103772-30-1 1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl]naphthalen-1-ol 

Relevant articles and documents

Simple synthesis and biological evaluation of flocoumafen and its structural isomers

Simple synthesis and biological properties of flocoumafen 1 and its structural isomers are described. The key synthetic strategies involve Knoevenagel condensation, Grignard reaction, intramolecular ring cyclization and coupling reaction. Flocoumafen 1 was easily separated into cis and trans forms using flash column chromatography. They were then evaluated for suppression of LPS-induced NO generation and anti-excitotoxicity in vitro. It was found that the trans-flocoumafen was potent suppressor of NO generation with the concentration of 10 μM in vitro, while no significant effect for neurotoxicity in cultured cortical neurons. Indian Academy of Sciences.

Separation of isomers

Process for selective removal of the cis-isomer and consequent enrichment of a solution with respect to the trans-isomer of a 1-(4-hydroxycoumarin-3-yl)-3-substituted phenyl)tetrahydronaphthalene rodenticide by crystallization from hot solvent.