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121-29-9

Basic Information
CAS No.: 121-29-9
Name: PYRETHRIN 2
Article Data: 4
Molecular Structure:
Molecular Structure of 121-29-9 (PYRETHRIN 2)
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
Synthetic route

C21H26O5

18107-18-1

diazomethyl-trimethyl-silane

121-29-9

Pyrethrin II

Conditions
ConditionsYield
With potassium carbonate In methanol; hexane; toluene at 20 - 25℃; for 16h; Inert atmosphere;46%
(1R)-2.2-dimethyl-3t-<2-methoxycarbonyl-cis-propenyl>-cyclopropane-carboxylic acid-(1r)-chloride

(1R)-2.2-dimethyl-3t-<2-methoxycarbonyl-cis-propenyl>-cyclopropane-carboxylic acid-(1r)-chloride

(+)-cis-pyrethrolone

(+)-cis-pyrethrolone

121-29-9

Pyrethrin II

27335-33-7

methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate

121-29-9

Pyrethrin II

Conditions
ConditionsYield
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

(S)-(+)-4-hydroxy-3-methyl-2-(pent-4-en-2-ynyl)-2-cyclopenten-1-one

121-29-9

Pyrethrin II

Conditions
ConditionsYield
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
487-67-2

(S)-(+)-pyrethrolone

121-29-9

Pyrethrin II

Conditions
ConditionsYield
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
Conditions
ConditionsYield
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
Conditions
ConditionsYield
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
4638-92-0

(1R,3R)-trans-chrysanthemic acid

121-29-9

Pyrethrin II

Conditions
ConditionsYield
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
77087-34-4

(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one

121-29-9

Pyrethrin II

Conditions
ConditionsYield
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
35867-05-1

methyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate

121-29-9

Pyrethrin II

Conditions
ConditionsYield
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
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Chemistry

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

Uses

 Pyrethrin II (CAS NO.121-29-9) can be used to produce aerosol insecticides, mosquito coils, animal shampoos and green pesticides.

Toxicity Data With Reference

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.


 

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

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 CodesHarmfulXn,DangerousN
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