56073-07-5

Basic information

• Product Name: Difenacoum
• Synonyms: RATAK;RIDAK;NEOSOREXA;1’-biphenyl)-4-yl-1,2,3,4-tetrahydro-1-naphthalenyl)-4-hydroxy-2h-1-3-(3-(;2h-1-benzopyran-2-one,3-(3-(1,1’-biphenyl)-4-yl-1,2,3,4-tetrahydro-1-naphtha;3-(3-(4-biphenylyl)-1,2,3,4-tetrahydro-1-naphthyl)-4-hydroxy-coumari;3-(3-(4-biphenylyl)-1,2,3,4-tetrahydro-1-naphthyl)-4-hydroxycoumarin;difenakum
• CAS NO: 56073-07-5
• Molecular Formula: C31H24O3
• Molecular Weight: 444.52
• EINECS: 259-978-4
• Product Categories: Agro-Products;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 56073-07-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 215-217°
• Boiling Point: 514.5°C (rough estimate)
• Flash Point: 257.538 °C
• Appearance: off-white powder
• Density: 1.0800 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• PKA: 4.50±1.00(Predicted)
• BRN: 8360065
• CAS DataBase Reference: Difenacoum(CAS DataBase Reference)
• NIST Chemistry Reference: Difenacoum(56073-07-5)
• EPA Substance Registry System: Difenacoum(56073-07-5)

Safety Data

• Hazard Codes: T+,N
• Statements: 28-48/25-50/53
• Safety Statements: 36/37-45-60-61
• RIDADR: 3027
• WGK Germany: 3
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 56073-07-5(Hazardous Substances Data)

Usage

Description

Difenacoum, is also called 3-(3-biphenyl-4-yl-1,2,3,4- tetrahydro-1-naphthyl)-4-hydroxycoumarin, consists of colorless crystals which are insoluble in water, moderately to readily soluble in acetone, chloroform, ethyl acetate, benzene.Difenacoum is synthesized by the condensation of 4-hydroxycoumarin and 3-biphenyl-4-yl-1,2,3,4-tetrahydro-1-naphthol (49).

Uses

Different sources of media describe the Uses of 56073-07-5 differently. You can refer to the following data:
1. Difenacoum is a 4-hydroxycouramin derivative. Difenacoum is a second generation anticoagulant rodenticide used against rodent pests such as rats and mice.
2. Pesticide.

Agricultural Uses

Rodenticide: Difenacoum is an anticoagulant that is effective against rats and mice, including warfarin-resistant strains. It is used in agriculture and urban rodent control as ready-to-use baits.

Trade name

COMPO?; MATRAK?; NEOSOREXA? PELLETS; NEOSOREXA PP580?; RASTOP?; RATAK?; RATRICK?; SILO; SOREXA GEL; STORM

Toxicity evaluation

Appearing in 1974, difenacoum was the first of the new generation of anticoagulants to be commercialized for the control of rodents resistant to warfarin and related compounds (42). LD50 values (acute oral) for warfarinsusceptible rodent strains are about a factor of 2 lower than for warfarin-resistant strains. There is also a degree of specificity. The compound is generally less toxic to nontarget animals than to targets. A wide range of bait types containing 0.005% difenacoum is available, including meals, broken and whole grains, pellets, and wax blocks. A 0.1% contact dust is no longer widely used. Resistance to difenacoum was detected among a population of Norway rats in the United Kingdom in 1978 (50). This remains a problem of local importance but relatively low resistance factors indicate that other behavioral factors also play a significant role (51). Difenacoum resistance has also been recorded in other European countries (39).

InChI:InChI=1/C31H24O3/c32-30-26-12-6-7-13-28(26)34-31(33)29(30)27-19-24(18-23-10-4-5-11-25(23)27)22-16-14-21(15-17-22)20-8-2-1-3-9-20/h1-17,24,27,32H,18-19H2

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 56181-66-9 (+/-)-cis/trans-3-(Biphenyl-4'-yl)-1,2,3,4-tetrahydronaphthalen-1-ol 
• 182511-13-3 (4R,5S)-1-((S)-3-Biphenyl-4-yl-4-phenyl-butyryl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 182511-11-1 (4R,5S)-1-((E)-3-Biphenyl-4-yl-acryloyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 81069-41-2 3-biphenyl-4-yl-acrylic acid ethyl ester 
• 13026-23-8 (2E)-3-(1,1'-biphenyl-4-yl)acrylic acid 
• 120301-61-3 (E)‐3‐([1,1'‐biphenyl]‐4‐yl)acryloyl chloride 
• 182356-06-5 (S)-3-([1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one 
• 182356-00-9 (4S,5R)-1-((R)-3-Biphenyl-4-yl-4-phenyl-butyryl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 182355-97-1 (4S,5R)-1-((E)-3-Biphenyl-4-yl-acryloyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 182356-02-1 (R)-3-([1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one 
• 56181-67-0 3-(1,1'-biphenyl)-4-yl-1-bromo-1,2,3,4-tetrahydronaphthalene 

Relevant articles and documents

Enantioselective rhodium-catalyzed hydroacylation to access the four stereoisomers of anti-rodent difenacoum

An efficient asymmetric synthesis of the four stereoisomers of difenacoum, an anticoagulant currently used as a rodenticide in racemic form, is performed using a key step of rhodium catalyzed enantioselective intramolecular hydroacylation. Optimization of the last step, condensation of 4-hydroxycoumarin with chiral 3-([1,1′-biphenyl]-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol, is also discussed. After chromatographic separation of the cis and trans diastereoisomers, the four stereoisomers were all obtained with excellent enantioselective and diastereoselective excess (ee?≈?96% and de >96%).

Efficient asymmetric synthesis of the four diastereomers of diphenacoum and brodifacoum

A highly stereo- and enantio-selective approach to the four stereoisomers of the rodenticides, diphenacoum and brodifacoum, is described. The key step involves the stereospecific formation of one of the crucial bonds in the molecular backbone, and is based on asymmetric organocopper 1,4-addition to chiral imides. Intramolecular cyclization of the resulting butanoate and coupling with 4-hydroxycoumarin, afford the title compounds.