5836-29-3 Usage
Description
Coumatetralyl, also known as 4-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthyl)coumarin, is a yellowish-white crystalline powder that is colorless when pure and odorless. It is a first-generation anticoagulant that was first introduced in 1956 and is widely used as a rodenticide.
Uses
Used in Pest Control Industry:
Coumatetralyl is used as an anticoagulant rodenticide for controlling rodent populations. It functions as an anticoagulant of the warfarin type that does not induce bait-shyness in rodents, making it an effective tool for rodent control.
Used in Agricultural Applications:
In agriculture, Coumatetralyl is used as a rat control agent. It serves as an anticoagulant rodenticide, helping to manage and reduce rat populations that can cause damage to crops and spread diseases.
Reactivity Profile
Ketones, such as Coumatetralyl, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Health Hazard
Overdosage with anticoagulants may cause acute bleeding. Pre-existing blood clotting disease or liver disease may be aggravated by exposure.
Fire Hazard
(Non-Specific -- Coumarin Derivative Pesticide, Solid, n.o.s.) Coumatetralyl may burn but does not ignite readily. Fire and runoff from fire control water may produce irritating or poisonous gases. Runoff from fire control water may give off poisonous gases. Container may explode in heat of fire. Enolic form of compound has acidic properties and can form salts with metals.
Trade name
BAY? 25634; BAY ENE? 11183B;
BAYER? 25,634; ENDOX?; ENDROCID?;
ENDROCIDE?; RACUMIN?; RAUCUMIN? 57;
RODENTIN?
Potential Exposure
Coumatetralyl is used as a rodenticide, functioning as an anticoagulant that does not induce baitshyness.
Shipping
UN3027 Coumarin derivative pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Toxicity evaluation
The acute toxicity
for Norway rats is given as high but, as with many of these compounds, coumatetralyl is more potent when administered
in consecutive daily doses. No satisfactory data are
available on the acute oral toxicity of the compound to mice.
However, a complete kill of mice was obtained in the laboratory
following 21 days of feeding on coumatetralyl bait (29).
Proprietary baits generally carry 0.375% coumatetralyl.
Powder concentrates are available (strength 0.75%) which
are used for the preparation of poisoned baits and as a
tracking dust (18).
Incompatibilities
Contact with oxidizers may cause fire and explosion hazard. Keep away from metals.
Waste Disposal
Dissolve in a solvent and burn in a furnace by spraying in the solution
Check Digit Verification of cas no
The CAS Registry Mumber 5836-29-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,8,3 and 6 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5836-29:
(6*5)+(5*8)+(4*3)+(3*6)+(2*2)+(1*9)=113
113 % 10 = 3
So 5836-29-3 is a valid CAS Registry Number.
InChI:InChI=1/C19H16O3/c20-18-15-9-3-4-11-16(15)22-19(21)17(18)14-10-5-7-12-6-1-2-8-13(12)14/h1-4,6,8-9,11,14,20H,5,7,10H2
5836-29-3Relevant articles and documents
Ionic Liquids with Multi-Active Sites Synergistically Catalyzed Metal-Free Transformation of Alcohols Using Dimethyl Carbonate as an Environmental Solvent
Li, Zengmin,Wen, Yating,Wang, Ning,Han, Feng,Li, Ying,Zhuang, Hongfeng,Miao, Chengxia
, p. 3819 - 3826 (2021/08/24)
One of the ultimate goals in organic synthesis is to develop metal-free, efficient and easily separable catalytic system for atom economic organic reactions in an environmental solvent. Direct substitution reaction of alcohols and hydrocarbon compounds is a significant and atom economic method for C?C bond formation. Herein, a metal-free and efficient catalytic system including recyclable pyridine-based ionic liquids with multiple active sites as the catalyst and dimethyl carbonate as the environmentally friendly solvent was developed for atom economic C3 substitution of 4-hydroxycoumarins with alcohols. Primary aromatic alcohols, secondary aliphatic and aromatic alcohols were suitable for the reaction, providing up to 99 % yield. The catalytic system could be easily scaled up to gram-scale with nearly quantitative yield. Coumatetralyl as commercial rodenticide could be prepared directly from commercially available 4-hydroxycoumarin and 1,2,3,4-tetrahydronaphthalen-1-ol. Racemic product derived from the reaction of (R)-1-phenylethanol and 4-hydroxycoumarin indicated the reaction was achieved through an SN1 pathway. The comparison of the activities and acidities of the ionic liquids demonstrated that there was no directly relationship between them. Control experiments showed that the reaction probably proceeded via carbocation, ether intermediate and synergistically promoted effect of hydrogen bonding between the ionic liquid with multi-active sites and substrates.
Alkylation of 1,3-dicarbonyl compounds with benzylic and propargylic alcohols using Ir-Sn bimetallic catalyst: Synthesis of fully decorated furans and pyrroles
Chatterjee, Paresh Nath,Roy, Sujit
experimental part, p. 4569 - 4577 (2011/07/08)
The heterobimetallic complex [Ir(COD)(SnCl3)Cl(μ-Cl)] 2 catalyzes the direct substitution of hydroxyl groups in benzylic and propargylic alcohols by 1,3-dicarbonyl moiety. In 4-hydroxycoumarin, benzylation and propargylation occurs at the 3-position. Selective propargylation or allenylation takes place depending on the nature of propargylic alcohol. By applying the methodology, multi-substituted furans and pyrroles have been synthesized in good yields.
Fe(ClO4)3·×H2O-Catalyzed direct C-C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles
Thirupathi, Ponnaboina,Kim, Sung Soo
experimental part, p. 2995 - 3003 (2010/06/14)
Fe(ClO4)3·×H2O as a highly effective catalyst for benzylation of 1,3-dikones, β-ketoesters, 1,3-diesters, electron-rich arenes and heteroarenes and 4-hydroxycoumarin with various benzylic alcohols is described. The usefulness of this procedure is shown by a synthesis of bis-symmetrical triarylmethanes and one step synthesis of an anti-coagulant compound 4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-2H-chromen-2-one (Coumatetralyl (B)). The advantages of this protocol are broad scope, mild conditions, use of inexpensive catalyst and simplicity of operation since water is the only side product.
