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CAS No.: | 121-29-9 |
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Name: | PYRETHRIN 2 |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C22H28 O5 |
Molecular Weight: | 372.461 |
Synonyms: | Cyclopropaneacrylicacid, 3-carboxy-a,2,2-trimethyl-,1-methyl ester, ester with4-hydroxy-3-methyl-2-(2,4-pentadienyl)-2-cyclopenten-1-one (7CI,8CI);Cyclopropanecarboxylic acid,3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-ylester, [1R-[1a[S*(Z)],3b(E)]]-; Cyclopropanecarboxylicacid, 3-[(1E)-3-methoxy-2-methyl-3-oxo-1-propenyl]-2,2-dimethyl-,(1S)-2-methyl-4-oxo-3-(2Z)-2,4-pentadienyl-2-cyclopenten-1-yl ester, (1R,3R)-(9CI); Pyrethrin II (6CI); (+)-Pyrethronyl (+)-pyrethrate; Biospray S;Pyrethrin; Pyrethrin 2; Pyrethrum mist |
EINECS: | 204-462-6 |
Density: | 1.12 g/cm3 |
Boiling Point: | 473.7 °C at 760 mmHg |
Flash Point: | 203.9 °C |
Hazard Symbols: | |
Risk Codes: | 20/21/22-50/53 |
Safety: | Poison experimentally by ingestion and intravenous routes. Moderately toxic to humans by unspecified route. An allergen. When heated to decomposition it emits acrid smoke and irritating fumes. An insecticide. See also PYRETHRIN; PYRETHRIN I; PYRETHRINS. |
PSA: | 69.67000 |
LogP: | 3.71130 |
Conditions | Yield |
---|---|
With potassium carbonate In methanol; hexane; toluene at 20 - 25℃; for 16h; Inert atmosphere; | 46% |
Pyrethrin II
methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate
Pyrethrin II
Conditions | Yield |
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Multi-step reaction with 5 steps 1.1: pyrrolidine / 1 h / 60 °C 2.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere 3.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 3.2: 2 h / 20 - 25 °C / Inert atmosphere 4.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 5.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
Pyrethrin II
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride; zinc / ethanol; water / 16 h / 75 - 80 °C / Inert atmosphere 2.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 2 h / 20 - 25 °C / Inert atmosphere 3.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 4.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 - 25 °C / Inert atmosphere 2.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 3.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
ethyl trans-(+/-)-chrysanthemate
Pyrethrin II
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: potassium hydroxide / ethanol; water / 3 h 2.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C 3.1: ozone / Acidic conditions 4.1: pyrrolidine / 1 h / 60 °C 5.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere 6.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 6.2: 2 h / 20 - 25 °C / Inert atmosphere 7.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 8.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
Pyrethrin II
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C 2.1: ozone / Acidic conditions 3.1: pyrrolidine / 1 h / 60 °C 4.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere 5.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 5.2: 2 h / 20 - 25 °C / Inert atmosphere 6.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 7.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: ozone / Acidic conditions 2.1: pyrrolidine / 1 h / 60 °C 3.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere 4.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 4.2: 2 h / 20 - 25 °C / Inert atmosphere 5.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 6.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
Pyrethrin II
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / toluene / 16 h / 20 - 25 °C / Inert atmosphere 2.1: hydrogenchloride; zinc / ethanol; water / 16 h / 75 - 80 °C / Inert atmosphere 3.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 3.2: 2 h / 20 - 25 °C / Inert atmosphere 4.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 5.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
methyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate
Pyrethrin II
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere 2.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 2 h / 20 - 25 °C / Inert atmosphere 3.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C 4.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere View Scheme |
IUPAC Name: [(1S)-2-Methyl-4-oxo-3-[(2Z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
Synonyms: (+)-Pyrethronyl(+)-pyrethrate ; 2-Methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl3-(3-methoxy-2-methyl-3-o ; 2-Methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-ylester ; 2-Methyl-4-oxo-3-(penta-2,4-dienyl)cyclopent-2-enyl3-(2-methoxycarbonylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate ; 3Beta(e)-*(z) ; 3Beta(e)-lpha[s(z)] ; Chrysanthemumdicarboxylicacidmonomethylesterpyrethroloneester ; Chrysanthemumdicarboxylicacidmonomethylesterpyrethroloneester
CAS NO: 121-29-9
Molecular Formula: C22H28O5
Molecular Weight: 371.44678
Molecular Structure:
EINECS: 204-462-6
Mol File: 121-29-9.mol
Index of Refraction: 1.528
Surface Tension: 40.7 dyne/cm
Density: 1.12 g/cm3
Flash Point: 203.9 °C
Enthalpy of Vaporization: 73.69 kJ/mol
Boiling Point: 473.7 °C at 760 mmHg
Vapour Pressure: 3.84E-09 mmHg at 25°C
Pyrethrin II (CAS NO.121-29-9) can be used to produce aerosol insecticides, mosquito coils, animal shampoos and green pesticides.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | LDLo | unreported | 1029mg/kg (1029mg/kg) | "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. | |
mouse | LD50 | oral | 130mg/kg (130mg/kg) | Agricultural and Biological Chemistry. Vol. 37, Pg. 2681, 1973. | |
rat | LD50 | intravenous | 1mg/kg (1mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Pesticide Biochemistry and Physiology. Vol. 2, Pg. 308, 1972. |
rat | LD50 | oral | 200mg/kg (200mg/kg) | Agricultural Research Service, USDA Information Memorandum. Vol. 20, Pg. 17, 1966. |
Reported in EPA TSCA Inventory.
Poison experimentally by ingestion and intravenous routes. Moderately toxic to humans by unspecified route. An allergen. When heated to decomposition it emits acrid smoke and irritating fumes. An insecticide. See also PYRETHRIN; PYRETHRIN I; PYRETHRINS.
Hazard CodesXn,N
Risk Statements 20/21/22-50/53
R20/21/22: Pyrethrin II (CAS NO.121-29-9) is harmful by inhalation, in contact with skin and if swallowed.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements 13-60-61
S13:Keep Pyrethrin II (CAS NO.121-29-9) away from food, drink and animal foodstuffs.
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR 2902
HazardClass 6.1(b)
PackingGroup III