Product Name

  • Name

    PYRETHRIN 2

  • EINECS 204-462-6
  • CAS No. 121-29-9
  • Article Data4
  • CAS DataBase
  • Density 1.12 g/cm3
  • Solubility
  • Melting Point
  • Formula C22H28 O5
  • Boiling Point 473.7 °C at 760 mmHg
  • Molecular Weight 372.461
  • Flash Point 203.9 °C
  • Transport Information
  • Appearance
  • 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.
  • Risk Codes 20/21/22-50/53
  • Molecular Structure Molecular Structure of 121-29-9 (PYRETHRIN 2)
  • Hazard Symbols
  • 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
  • PSA 69.67000
  • LogP 3.71130

Synthetic route

C21H26O5

C21H26O5

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

Pyrethrin II
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

Pyrethrin II
121-29-9

Pyrethrin II

methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate
27335-33-7

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

Pyrethrin II
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

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

Pyrethrin II
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
(S)-(+)-pyrethrolone
487-67-2

(S)-(+)-pyrethrolone

Pyrethrin II
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
ethyl trans-(+/-)-chrysanthemate
97-41-6, 1802-02-4, 7377-84-6, 15543-65-4, 16642-27-6, 34909-55-2, 41641-25-2, 41641-26-3, 41641-27-4

ethyl trans-(+/-)-chrysanthemate

Pyrethrin II
121-29-9

Pyrethrin II

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
trans-chrysanthemic acid
827-90-7, 2259-14-5, 2935-23-1, 4638-92-0, 10453-89-1, 15259-78-6, 26771-06-2, 26771-11-9, 705-16-8

trans-chrysanthemic acid

Pyrethrin II
121-29-9

Pyrethrin II

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
(1R,3R)-trans-chrysanthemic acid
4638-92-0

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

Pyrethrin II
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
(S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one
77087-34-4

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

Pyrethrin II
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
methyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate
35867-05-1

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

Pyrethrin II
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
(1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid

(1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid

Pyrethrin II
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
C21H26O4

C21H26O4

Pyrethrin II
121-29-9

Pyrethrin II

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C
2: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere
View Scheme
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

Pyrethrin II
121-29-9

Pyrethrin II

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium hydride / mineral oil / 3 h / Inert atmosphere
2.1: potassium hydroxide / ethanol; water / 3 h
3.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C
4.1: ozone / Acidic conditions
5.1: pyrrolidine / 1 h / 60 °C
6.1: potassium hydroxide / water; methanol; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 20 - 25 °C / Inert atmosphere
7.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
7.2: 2 h / 20 - 25 °C / Inert atmosphere
8.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 5 h / 20 - 25 °C
9.1: potassium carbonate / hexane; toluene; methanol / 16 h / 20 - 25 °C / Inert atmosphere
View Scheme
Pyrethrin II
121-29-9

Pyrethrin II

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; for 4h;97%
Pyrethrin II
121-29-9

Pyrethrin II

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; stereoselective reaction;20%
Pyrethrin II
121-29-9

Pyrethrin II

A

8',9'-epoxypyrethrin II

8',9'-epoxypyrethrin II

B

10',11'-epoxypyrethrin II

10',11'-epoxypyrethrin II

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1.5h;A 19%
B 7%
Pyrethrin II
121-29-9

Pyrethrin II

A

(S)-2-methyl-4-oxo-3-(penta-1,3-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

(S)-2-methyl-4-oxo-3-(penta-1,3-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

B

(1S)-2-methyl-4-oxo-3-((E)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

(1S)-2-methyl-4-oxo-3-((E)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
With formic acid; palladium 10% on activated carbon In tetrahydrofuran for 5h; Inert atmosphere; Reflux;A 19%
B 14%
Pyrethrin II
121-29-9

Pyrethrin II

acetic acid
64-19-7

acetic acid

A

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

B

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

C

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
Stage #1: Pyrethrin II With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran for 5h; Inert atmosphere;
Stage #2: acetic acid In tetrahydrofuran for 1h; Inert atmosphere; Reflux;		A n/a
B n/a
C 19%
...Expand
Pyrethrin II
121-29-9

Pyrethrin II

(-) trans-chrysanthemum dicarboxylic acid
72120-98-0

(-) trans-chrysanthemum dicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol Hydrolysis;
Pyrethrin II
121-29-9

Pyrethrin II

A

7',8'-epoxypyrethrin II

7',8'-epoxypyrethrin II

B

7',8'-dihyroxypyrethrin II

7',8'-dihyroxypyrethrin II

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In benzene at 64℃; for 24h;A n/a
B 14 mg
Pyrethrin II
121-29-9

Pyrethrin II

8',9'-dihydroxypyrethrin II

8',9'-dihydroxypyrethrin II

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h
2: water; sulfuric acid / methanol / 1 h / 20 °C
View Scheme
Pyrethrin II
121-29-9

Pyrethrin II

A

(1S,4S)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4S)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

B

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4R)-4-hydroxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 3h;A 40 mg
B 163 mg
Pyrethrin II
121-29-9

Pyrethrin II

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4R)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / Inert atmosphere
1.2: 1 h / Inert atmosphere; Reflux
2.1: triethylamine / dichloromethane / 4.5 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 2 steps
1: L-Selectride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4.5 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 3 h / 0 °C
2: triethylamine / dichloromethane / 4.5 h / Inert atmosphere; Reflux
View Scheme
Pyrethrin II
121-29-9

Pyrethrin II

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

(1S,4S)-4-acetoxy-2-methyl-3-((2Z)-penta-2,4-dien-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 3 h / 0 °C
2: triethylamine / dichloromethane / 4.5 h / Inert atmosphere; Reflux
View Scheme
Pyrethrin II
121-29-9

Pyrethrin II

A

(S)-2-methyl-4-oxo-3-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
1172-63-0

(S)-2-methyl-4-oxo-3-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

B

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

(1S)-2-methyl-4-oxo-3-pentylcyclopent-2-en-1-yl (1R,3R)-3-((E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; hydrazine hydrate; acetic acid In tetrahydrofuranA 66 %Chromat.
B 26 %Chromat.

PYRETHRIN II Chemical Properties

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 Uses

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

PYRETHRIN II 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.


 

PYRETHRIN II Consensus Reports

Reported in EPA TSCA Inventory.

PYRETHRIN II 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
 

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