Allethrin CAS 584-79-2
Introduction：Basic information about Allethrin CAS 584-79-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Allethrin Basic information
| Product Name: | Allethrin |
| Synonyms: | (.+/-.)-3-Allyl-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropylcarboxylate;2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylicaciesterwith2-a;BIOALLETHRINE;BIOALLETHRIN;D-TRANS;(+-)-3-allyl-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(2-methylpropen-1-yl)cyclopropanecarboxylate;(R,S)-3-ally-2-methyl-4-oxo-cyclopent-2-enyl-(1R)-chrysanthemate;ALLETHRIN MIXTURE OF STEREO ISOMERS, PES |
| CAS: | 584-79-2 |
| MF: | C19H26O3 |
| MW: | 302.41 |
| EINECS: | 209-542-4 |
| Product Categories: | Pharmaceutical intermediates;HERBICIDE;INSECTICIDE;Endocrine Disruptors (Draft)Fluorescent Probes, Labels, Particles and Stains;Other Fluorescent LabelsPesticides;A;AA to ALMethod Specific;Alphabetic;EPA;Fluorescent Labels;A-BAlphabetic;Alpha sort;B;BI - BZPesticides;Insecticides;Pesticides&Metabolites;Pyrethroids |
| Mol File: | 584-79-2.mol |
Allethrin Chemical Properties
| Melting point | approximate 4℃ |
| Boiling point | 160°C |
| density | 1.01 |
| vapor pressure | 1.6×10-4 Pa (21 °C) |
| refractive index | nD20 1.5040; nD30 1.5023 |
| Fp | 66 °C |
| storage temp. | 2-8°C |
| solubility | Chloroform: Slightly Soluble |
| Water Solubility | 2 mg l-1 |
| form | Viscous Liquid |
| color | Clear amber |
| BRN | 2294836 |
| InChI | 1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3 |
| InChIKey | ZCVAOQKBXKSDMS-UHFFFAOYSA-N |
| SMILES | C\C(C)=C\[C@@H]1[C@@H](C(=O)O[C@H]2CC(=O)C(CC=C)=C2C)C1(C)C |
| LogP | 4.780 |
| CAS DataBase Reference | 584-79-2(CAS DataBase Reference) |
| NIST Chemistry Reference | Bioallethrin(584-79-2) |
| EPA Substance Registry System | Allethrin (584-79-2) |
Safety Information
| Hazard Codes | Xn;N,N,Xn |
| Risk Statements | 20/22-50/53-40 |
| Safety Statements | 36-60-61-36/37-24/25-23 |
| RIDADR | UN 3082 |
| WGK Germany | 3 |
| RTECS | GZ1925000 |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29183000 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Acute Tox. 4 Inhalation Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 584-79-2(Hazardous Substances Data) |
| Toxicity | LD50 oral in rabbit: 4290mg/kg |
| Chemical Properties | Yellow Oil |
| Uses | Allethrin is a synthetic pyrethroid derivative used as an insecticide. Allethrin is commonly used in many household insecticide products due to its low toxicity towards humans. |
| Uses | The allethrins are used to control a wide range of insects in horticultural,household, public health and animal health situations. Theyhave some limited use on ornamentals and vegetables (in combinationwith synergists). |
| Uses | Esbiothrin may be used as a reference standard for the determination of the analyte in electric-mosquito coils using gas chromatography (GC) technique. |
| Definition | Generic name for 2-allyl4-hydroxtcyclopenten-1-one ester of chrysanthemummonocarboxylic acid. A synthetic insecticide structurally similar to pyrethrin and used in the same manner. For other synthetic analogs, see barthrin, cyclethrin, ethythrin, furethrin. Pyrethrin I differs in having a 2,4-pentadienyl group in place of the allyl of allethrin. |
| General Description | A clear amber-colored viscous liquid. Insoluble and denser than water. Toxic by ingestion, inhalation, and skin absorption. A synthetic household insecticide that kills flies, mosquitoes, garden insects, etc. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Allethrin is an ester and ketone. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Ketones 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 | Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. |
| Fire Hazard | Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. |
| Agricultural Uses | Insecticide: Allethrin is used almost exclusively to control flying and crawling insects in homes and industrial locations.Used extensively in pet animal shampoos, to treat lice inhumans and in home and industrial sprays for flying insects, mosquitos, etc. It is available as mosquito coils,mats, oil formulations and as an aerosol spray. It may behazardous to the environment; special attention should begiven to fish and honey bees. Not currently registered in theU.S. Not approved for use in EU countries. Dependingon CAS registry number there are probably >100 globalsuppliers. |
| Trade name | BIOALLETHRIN®; BIOALLETHRINTECHNICAL®; d-CISALLETHRIN®; ESBIOTHRIN®;EXTHRIN® FMC 249®; NIA 249®; OMS 468®;PYNAMIN®; PYNAMIN-FORTE®; PYRESIN®;PYRESYN®; PYREXCEL®; PYROCIDE®; SBP 1382/BIOALLETHRIN CONCENTRATE® |
| Contact allergens | Pyrethroids, also called pyrethrinoids, are neurotoxicsynthetic compounds used as insecticides, with irritantproperties. Cypermethrin and fenvalerate have beenreported as causing positive allergic patch tests, butonly fenvalerate was relevant in an agricultural worker. |
| Safety Profile | Poison by intravenous, intracerebral, and intraperitoneal routes. Moderately toxic by ingestion and skin contact. An allergen. An insecticide. It can cause liver and kidney damage by all routes of entry into the body. Lung congestion may occur due to exposure. Local contact may cause contact dermatitis. Inhalation may cause asthma, coughing, wheezing, running nose and eyes. Mutation data reported. See also ALLYL COMPOUNDS and ESTERS. Slight fire hazard. When heated to decomposition it emits acrid fumes. |
| Metabolic pathway | Allethrin was the first synthetic pyrethroid. Its stereochemistry isRS(cyclopentenyl)lRcis-trans. It was further developed as bioallethrin(RSlRtvuns) and then as S-bioallethrin (SlRtvuns), the most potent of thethree. All are very sensitive to light and are used almost entirely indoors.Thus, there is only a limited amount of information on their environmentalfate published in the literature. Information on photodegradationand on metabolism in insects and rodents has been reported. |
| Degradation | The allethrins are reasonably stable but they are sensitive to basehydrolysis forming chrysanthemic acid (2) and 3-allyl-2-methyl-4-oxocyclopent-2-enol(3, allethrolone). The DT50 of bioallethrin in aqueoussolution is 547 days at pH 7 and 4.3 days at pH 9. The allethrins are also sensitive to oxidation and to photodecomposition.Allethrin was converted almost quantitatively into thecycloproprethronyl derivative (4) by a di-π-methane rearrangement onirradiation in hexane solution (Bullivant and Pattenden, 1976). Inaddition, isomerisation, oxidation and epoxidation of the isobutenylgroup of the chrysanthemic acid moiety by reactions analogous to thosedescribed under phenothrin have been described (Ruzo et al., 1980).Most products retained the ester linkage but the acid 2 was identified.A novel product, 1-cyclopropyl-5-methyl-6-oxabicyclo[3.0.1]hexan-2-on-4-yl chrysanthemate (5), was then reported (Kimmel et al., 1982). Thisproduct proved to be a potent bacterial mutagen (Ames assay). LaterIsobe et al. (1984) reported photo-oxidation products derived from thealcohol moiety: the alcohol (3) and allethronyl glyoxalate (6). Thelatter was mostly present as its hydrate (7).T he ester (8) was also detectedbut this was shown not to be a precursor of 6 or 7. These productsare illustrated in Scheme 1. Products formed by oxidation of the acidmoiety and retaining the ester link, such as 9, 10 and 11, are shown inScheme 2. These two sites of weakness in allethrin render it one of the most photolabileof the synthetic pyrethroids (Ruzo, 1982) and result in a complexmixture of degradation products. |
Allethrin Preparation Products And Raw materials
| Raw materials | Chloral-->Cyclopentanone-->2-Methylfuran-->Ethyl chrysanthemumate-->3-Furaldehyde-->Chrysanthemoyl chloride-->TRANS-(+)-CHRYSANTHEMIC ACID-->rich_d_transallethrin-->Conversion catalyst-->D-trans-Allethrin |
