Product Name

  • Name

    Pyriproxyfen

  • EINECS 429-800-1
  • CAS No. 95737-68-1
  • Article Data5
  • CAS DataBase
  • Density 1.151 g/cm3
  • Solubility 0.4 mg l-1 (25 °C)
  • Melting Point 45-47 °C
  • Formula C20H19NO3
  • Boiling Point 462 °C at 760 mmHg
  • Molecular Weight 321.376
  • Flash Point 165.4 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance White to pale yellow crystalline powder
  • Safety 60-61
  • Risk Codes 50/53
  • Molecular Structure Molecular Structure of 95737-68-1 (Pyriproxyfen)
  • Hazard Symbols DangerousN
  • Synonyms Pyriproxyfen [ISO:BSI];S 9138;Pyridine, 2-(1-methyl-2-(4-phenoxyphenoxy)ethoxy)- .;2-(1-Methyl-2-(4-phenoxyphenoxy)ethoxy)pyridine;4-Phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether;HSDB 7053;OMS 3019;SK 591;
  • PSA 40.58000
  • LogP 4.72020

Synthetic route

2-chloropyridine
109-09-1

2-chloropyridine

(R,S)-2-hydroxypropyl 4-phenoxyphenyl ether
57650-78-9

(R,S)-2-hydroxypropyl 4-phenoxyphenyl ether

pyriproxyfen
95737-68-1

pyriproxyfen

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 50 - 110℃; Solvent; Temperature; Reagent/catalyst;93.9%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

pyriproxyfen
95737-68-1

pyriproxyfen

C32H26NO3S2(1+)*BF4(1-)

C32H26NO3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; pyriproxyfen With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube;
Stage #2: sodium tetrafluoroborate In dichloromethane; water
95%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

2,3,7,8-tetrafluorothianthrene-S-oxide

2,3,7,8-tetrafluorothianthrene-S-oxide

pyriproxyfen
95737-68-1

pyriproxyfen

C32H22F4NO3S2(1+)*BF4(1-)

C32H22F4NO3S2(1+)*BF4(1-)

Conditions
ConditionsYield
With 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction;92%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

2,3,7,8-tetrafluorothianthrene-S-oxide

2,3,7,8-tetrafluorothianthrene-S-oxide

pyriproxyfen
95737-68-1

pyriproxyfen

C32H22F4NO3S2(1+)*BF4(1-)

C32H22F4NO3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; 2,3,7,8-tetrafluorothianthrene-S-oxide; pyriproxyfen With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube;
Stage #2: sodium tetrafluoroborate In dichloromethane; water
92%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

triphenylphosphine
603-35-0

triphenylphosphine

pyriproxyfen
95737-68-1

pyriproxyfen

(2-((1-(4-phenoxyphenoxy)propan-2-yl)oxy)pyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate

(2-((1-(4-phenoxyphenoxy)propan-2-yl)oxy)pyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate

Conditions
ConditionsYield
at -78 - 20℃; Alkaline conditions;89%
Stage #1: trifluoromethylsulfonic anhydride; pyriproxyfen In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: triphenylphosphine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -78 - 20℃; Inert atmosphere; regioselective reaction;
61%
acetophenone
98-86-2

acetophenone

pyriproxyfen
95737-68-1

pyriproxyfen

1-phenyl-2-(4-(4-(2-(pyridin-2-yloxy)propoxy)phenoxy)phenyl)ethan-1-one

1-phenyl-2-(4-(4-(2-(pyridin-2-yloxy)propoxy)phenoxy)phenyl)ethan-1-one

Conditions
ConditionsYield
Stage #1: pyriproxyfen With thianthrene-5-oxide; trifluoromethylsulfonic anhydride In acetonitrile at -20 - 20℃; for 0.666667h; Inert atmosphere; Schlenk technique;
Stage #2: acetophenone With palladium diacetate; cesium fluoride; XPhos In N,N-dimethyl-formamide; acetonitrile at 80℃; for 11h; Inert atmosphere; Schlenk technique; regioselective reaction;
84%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2,8-dimethoxydibenzothiophene S-oxide

2,8-dimethoxydibenzothiophene S-oxide

pyriproxyfen
95737-68-1

pyriproxyfen

C34H30NO5S(1+)*CF3O3S(1-)

C34H30NO5S(1+)*CF3O3S(1-)

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at -40 - 25℃; for 2h; Schlenk technique; Glovebox; Inert atmosphere;45%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

pyriproxyfen
95737-68-1

pyriproxyfen

C26H23FNO3(1+)*CF3O3S(1-)

C26H23FNO3(1+)*CF3O3S(1-)

Conditions
ConditionsYield
Stage #1: 4-methylphenylboronic acid With copper(II) bis(trifluoromethanesulfonate) In toluene for 1h; Inert atmosphere; Glovebox;
Stage #2: pyriproxyfen In toluene at 90℃; for 16h; Inert atmosphere; Sealed tube;
6%
pyriproxyfen
95737-68-1

pyriproxyfen

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

1.3C36H60O30*C20H19NO3

1.3C36H60O30*C20H19NO3

Conditions
ConditionsYield
In water at 20 - 50℃; for 26h;
pyriproxyfen
95737-68-1

pyriproxyfen

4-phenoxyphenyl 2-(2-pyridyloxy)propyl ether

4-phenoxyphenyl 2-(2-pyridyloxy)propyl ether

4-phenoxyphenyl 2-(2-pyridyloxy)propyl ether

4-phenoxyphenyl 2-(2-pyridyloxy)propyl ether

Conditions
ConditionsYield
With Chiralpak IC In water; acetonitrile at 15℃; Solvent; Reagent/catalyst; Resolution of racemate;
pyriproxyfen
95737-68-1

pyriproxyfen

2-((1-(4-phenoxyphenoxy)propan-2-yl)oxy)pyridine-4-d

2-((1-(4-phenoxyphenoxy)propan-2-yl)oxy)pyridine-4-d

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 0.5 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
1.3: -78 - 20 °C / Inert atmosphere
2.1: d(4)-methanol; water-d2; potassium carbonate / 2 h / 20 °C / Inert atmosphere
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

cyclopropylpyriproxyfen

cyclopropylpyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / tetrahydrofuran / 50 °C
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

methylpyriproxyfen

methylpyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / tetrahydrofuran / 50 °C
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

hexynylpyriproxyfen

hexynylpyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 4-methyl-morpholine / 1,4-dioxane / 40 °C
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

C28H31NO3

C28H31NO3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / ethanol / 50 °C
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

carboxyethylpyriproxyfen

carboxyethylpyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 4-methyl-morpholine / 1,4-dioxane / 50 °C / 750.08 Torr
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

2-((1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)phenoxy)propan-2-yl)oxy)pyridine

2-((1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)phenoxy)propan-2-yl)oxy)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; pyridine / acetonitrile / 22 °C / Irradiation
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 1 h / -40 - 20 °C
2: dmap; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile / acetonitrile / 8 h / 20 °C / Irradiation; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 1.5 h / -40 - 20 °C / Schlenk technique; Inert atmosphere
2: palladium diacetate; XPhos; sodium pivalate / acetone; dichloromethane / 12 h / 20 °C / Inert atmosphere
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

C32H28NO6P

C32H28NO6P

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; pyridine; sodium iodide / acetonitrile / 22 °C / Irradiation
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

cyanopyriproxyfen

cyanopyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrakis(acetonitrile)copper(I)tetrafluoroborate / acetonitrile / 22 °C / Irradiation
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

2-((1-(4-(4-((trifluoromethyl)thio)phenoxy)phenoxy)propan-2-yl)oxy)pyridine

2-((1-(4-(4-((trifluoromethyl)thio)phenoxy)phenoxy)propan-2-yl)oxy)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrakis(acetonitrile)copper(I)tetrafluoroborate / acetonitrile / 22 °C / Irradiation
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

chloropyriproxyfen

chloropyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; copper(l) chloride; tetrabutyl-ammonium chloride / acetonitrile / 22 °C / Irradiation
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

iodopyriproxyfen

iodopyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrakis(acetonitrile)copper(I)tetrafluoroborate; lithium iodide / acetonitrile; dimethyl sulfoxide / 22 °C / Irradiation
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

styrenylpyriproxyfen

styrenylpyriproxyfen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride / acetonitrile / 0 - 25 °C
2: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 100 °C
View Scheme
pyriproxyfen
95737-68-1

pyriproxyfen

C24H27NO3

C24H27NO3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: -78 - 20 °C / Alkaline conditions
2: cobalt(III) acetylacetonate; C22H28N2O2; 1-methyl-1H-imidazole / tetrahydrofuran / 12 h / 23 °C
View Scheme
thianthrene-5-oxide
2362-50-7

thianthrene-5-oxide

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

pyriproxyfen
95737-68-1

pyriproxyfen

C32H26NO3S2(1+)*CF3O3S(1-)

C32H26NO3S2(1+)*CF3O3S(1-)

Conditions
ConditionsYield
In dichloromethane at -40 - 20℃; for 1h;
In dichloromethane at -40 - 20℃; Inert atmosphere; Schlenk technique;
In dichloromethane at -40 - 20℃; for 1.5h; Schlenk technique; Inert atmosphere;
In dichloromethane at -40 - 20℃; for 0.333333h; Schlenk technique; Inert atmosphere; regioselective reaction;
pyriproxyfen
95737-68-1

pyriproxyfen

C20H19NO4

C20H19NO4

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 18h;
pyriproxyfen
95737-68-1

pyriproxyfen

C28H25NO5

C28H25NO5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / -40 - 20 °C / Inert atmosphere; Schlenk technique
2: sodium hydrogencarbonate; bis(tri-t-butylphosphine)palladium(0) / dichloromethane; acetone / 12 h / 50 °C / Inert atmosphere; Schlenk technique; Sealed tube
View Scheme
ethyl 2-((trifluoromethyl)sulfinyl)acetate

ethyl 2-((trifluoromethyl)sulfinyl)acetate

pyriproxyfen
95737-68-1

pyriproxyfen

C25H25F3NO5S(1+)

C25H25F3NO5S(1+)

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride In nitromethane at -25 - 20℃; for 3.16667h; Inert atmosphere;

Pyriproxyfen Chemical Properties

Molecular structure of Pyriproxyfen (CAS NO.95737-68-1) is:

Product Name: Pyriproxyfen
CAS Registry Number: 95737-68-1
IUPAC Name: 2-[1-(4-Phenoxyphenoxy)propan-2-yloxy]pyridine
Molecular Weight: 321.36976 [g/mol]
Molecular Formula: C20H19NO3
XLogP3-AA: 4.8
H-Bond Donor: 0
H-Bond Acceptor: 4 
EINECS: 429-800-1
Melting Point: 45-47 °C
Storage temp.: 0-6°C 
Surface Tension: 43.8 dyne/cm
Density: 1.151 g/cm3
Flash Point: 165.4 °C
Enthalpy of Vaporization: 69.52 kJ/mol
Boiling Point: 462 °C at 760 mmHg
Vapour Pressure: 2.83E-08 mmHg at 25°C
Product Categories: Pesticide & intermediate; Insect hormone

Pyriproxyfen Uses

 Pyriproxyfen (CAS NO.95737-68-1) can be used to protect other crops and also be used as a treatment for cat fleas. It is a juvenile hormone analogue, preventing larvae from developing into adulthood and thus rendering them unable to reproduce.

Pyriproxyfen Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 9, Pg. 745, 1991.
rat LD50 skin > 2gm/kg (2000mg/kg)   Pesticide Manual. Vol. 9, Pg. 745, 1991.

Pyriproxyfen Safety Profile

Safty information about Pyriproxyfen (CAS NO.95737-68-1) is:
Hazard Codes: DangerousN
Risk Statements: 50/53 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 60-61 
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: UN3077 9/PG 3
RTECS: UT5804000

Pyriproxyfen Specification

 Pyriproxyfen , its cas register number is 95737-68-1. It also can be called Pyriproxyfen [ISO:BSI] ; S 31183 ; 2-(1-Methyl-2-(4-phenoxyphenoxy)ethoxy)pyridine ; 4-Phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether ; HSDB 7053 ; OMS 3019 ; S 9138 ; SK 591 ; Pyridine, 2-(1-methyl-2-(4-phenoxyphenoxy)ethoxy)- . It is a colorless crystals. It is a pyridine based pesticide which is found to be effective against a variety of arthropoda.

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