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Permethrin

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Name

Permethrin

EINECS 258-067-9
CAS No. 52645-53-1 Density 1.293 g/cm3
PSA 35.53000 LogP 6.11330
Solubility insoluble in water Melting Point 34-35 °C
Formula C21H20Cl2O3 Boiling Point 465.9 °C at 760 mmHg
Molecular Weight 391.294 Flash Point 159.4 °C
Transport Information UN1230 3/PG 2 Appearance Crystalline Solid
Safety 13-24-36/37/39-60-61-45-36/37-16-7-26 Risk Codes 20/22-43-50/53-39/23/24/25-23/24/25-11-51/53-36-20/21/22
Molecular Structure Molecular Structure of 52645-53-1 (Permethrin) Hazard Symbols HarmfulXn, DangerousN, ToxicT, FlammableF
Synonyms

Corsair;InsomniaInsorbcid MP;Ecsumin;Dragnet;Ectiban;Cyclopropanecarboxylic acid,3-(2,2-dichloroethenyl)-2,2-dimethyl-,(3-phenoxyphenyl)methyl ester;Riapan A;NIA 33297;S 3151;FMC 41655;Exmin;SBP 15131TEC;Damminix;Perigen;Perigen W;KaleCollards are also indexed at this headingKaleait;Pounce;Stomoxys calcitransStablefly is also indexed at this headingStomozan;MP 79;KestrelThis heading is used only when the specific taxonomycannot be established from the original documentKestrel (pesticide);NRDC 143;Chinetrin;Pertrin E;Imperator;Kavil;Bematin 987;JF 7065;ICI-PP 557;Anomethrin N;WL 43479;Kudos;Permasect;FMC 33297;m-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate;Permethrin;

Article Data 34

Permethrin Synthetic route

2,2-Dimethyl-3-(2,2,2-trichloro-ethyl)-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester

52645-53-1

permethrin

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene Heating;100%
2304-30-5

tetra-n-butylphosphonium chloride

13826-35-2

3-Phenoxybenzyl alcohol

63142-59-6

4-(2,2-dichloroethenyl)dihydro-5,5-dimethyl-2(3H)-furanone

52645-53-1

permethrin

Conditions
ConditionsYield
With potassium hydroxide; thionyl chloride In ice-water; toluene; benzene95%
61898-95-1

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate

13826-35-2

3-Phenoxybenzyl alcohol

A

(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-chloroethynyl)cyclopropanecarboxylate

B

52645-53-1

permethrin

Conditions
ConditionsYield
With lithium methanolate In methanol; xylene at 100 - 145℃; for 12h; Heating / reflux;A 0.1%
B 94%
With sodium methylate In methanolA 1.1%
B 81%
52314-67-7

permethric acid chloride

13826-35-2

3-Phenoxybenzyl alcohol

52645-53-1

permethrin

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction;93%
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 25℃; for 2h;92%
60066-52-6

3-phenoxybenzyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate

52645-53-1

permethrin

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran75%
13826-35-2

3-Phenoxybenzyl alcohol

52645-53-1

permethrin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 0.83 h / -78 - 20 °C
2: 100 percent / DBU / benzene / Heating
View Scheme
pyridine In benzene

[2,2-Dimethyl-3-(2,2,2-trichloro-ethyl)-cyclopropyl]-hydroxy-acetonitrile

52645-53-1

permethrin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 15 min
2: CH2Cl2 / 0.83 h / -78 - 20 °C
3: 100 percent / DBU / benzene / Heating
View Scheme

[2,2-Dimethyl-3-(2,2,2-trichloro-ethyl)-cyclopropyl]-oxo-acetonitrile

52645-53-1

permethrin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 0.83 h / -78 - 20 °C
2: 100 percent / DBU / benzene / Heating
View Scheme
546-68-9

titanium(IV) isopropylate

61898-95-1

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate

13826-35-2

3-Phenoxybenzyl alcohol

52645-53-1

permethrin

Conditions
ConditionsYield
With nitrogen
61898-95-1

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate

13826-35-2

3-Phenoxybenzyl alcohol

52645-53-1

permethrin

Permethrin Chemical Properties


IUPAC Name: (3-phenoxyphenyl)methyl(1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Molecular Formula: C21H20Cl2O3
Molecular Weight: 391.29 g/mol
EINECS: 258-067-9
Classification Code: Agricultural Chemical; Ectoparasiticide; Enzyme Inhibitors; Human Data; Insecticide; Insecticides; Mutation data; Pesticides; Reproductive Effect; Skin / Eye Irritant; Tumor data
Index of Refraction: 1.615
Molar Refractivity: 105.69 cm3
Molar Volume: 302.5 cm3
Surface Tension: 50.5 dyne/cm
Density: 1.293 g/cm3
Flash Point: 159.4 °C
Enthalpy of Vaporization: 72.76 kJ/mol
Boiling Point: 465.9 °C at 760 mmHg
Melting Point: 34-35 °C
storage temperature: 0-6 °C
Water Solubility: insoluble
Stability: Stable. Incompatible with strong oxidising agents.
Vapour Pressure of Permethrin (CAS NO.52645-53-1): 7.41E-09 mmHg at 25 °C

Permethrin Uses

  Permethrin (CAS NO.52645-53-1) is used as synthetic pyrethroid insectide, more stable to light and at least as active as the natural pyrethrins and with low mammalian toxicity.

Permethrin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LD50 oral 32gm/kg (32000mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
chicken LD50 oral 7gm/kg (7000mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: IRRITABILITY

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
JAT, Journal of Applied Toxicology. Vol. 7, Pg. 367, 1987.
duck LD50 oral 11300mg/kg (11300mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
guinea pig LD50 oral 4gm/kg (4000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A316, Pg. 1984,
man LD50 unreported > 4gm/kg (4000mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
man TDLo oral 2270mg/kg (2270mg/kg) BEHAVIORAL: COMA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Journal of Toxicology, Clinical Toxicology. Vol. 36, Pg. 57, 1998.
mouse LC50 inhalation 685mg/m3 (685mg/m3)   Yakkyoku. Pharmacy. Vol. 30, Pg. 1635, 1979.
mouse LD50 intraperitoneal 429mg/kg (429mg/kg)   Ecotoxicology and Environmental Safety. Vol. 18, Pg. 27, 1989.
mouse LD50 intravenous 31mg/kg (31mg/kg)   Toxicology and Applied Pharmacology. Vol. 66, Pg. 153, 1982.
mouse LD50 oral 424mg/kg (424mg/kg)   Ecotoxicology and Environmental Safety. Vol. 18, Pg. 27, 1989.
mouse LD50 skin > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 1635, 1979.
mouse LD50 subcutaneous 10gm/kg (10000mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
Bochu Kagaku. Scientific Pest Control. Vol. 41, Pg. 143, 1976.
mouse LD50 unreported 680mg/kg (680mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

BEHAVIORAL: ATAXIA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.
mouse LDLo intracrebral 600ug/kg (0.6mg/kg)   Toxicology and Applied Pharmacology. Vol. 66, Pg. 290, 1982.
quail LD50 oral 13500mg/kg (13500mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
rabbit LD50 oral 4gm/kg (4000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A316, Pg. 1984,
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C233, 1991.
rat LC50 inhalation 485mg/m3 (485mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(12), Pg. 21, 1990.
rat LD intravenous > 270mg/kg (270mg/kg)   Nature. Vol. 246, Pg. 169, 1973.
rat LD50 oral 383mg/kg (383mg/kg)   National Technical Information Service. Vol. AD-A047-284,
rat LD50 skin 1750mg/kg (1750mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.
rat LD50 subcutaneous 6600mg/kg (6600mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
Bochu Kagaku. Scientific Pest Control. Vol. 41, Pg. 143, 1976.
rat LD50 unreported 537mg/kg (537mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

BEHAVIORAL: COMA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.

Permethrin Safety Profile

Poison by inhalation, intravenous, and intracerebral routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of Cl. See also ESTERS.
Hazard Codes: HarmfulXn,DangerousN,ToxicT,FlammableF
Risk Statements: 20/22-43-50/53-39/23/24/25-23/24/25-11-51/53-36-20/21/22 
R20/22:Harmful by inhalation and if swallowed. 
R43:May cause sensitization by skin contact. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R39:Danger of very serious irreversible effects. 
R11:Highly flammable. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R36:Irritating to eyes. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 13-24-36/37/39-60-61-45-36/37-16-7-26 
S13:Keep away from food, drink and animal foodstuffs. 
S24:Avoid contact with skin. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
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. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37:Wear suitable protective clothing and gloves. 
S16:Keep away from sources of ignition. 
S7:Keep container tightly closed. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN1230 3/PG 2
RTECS: GZ1255000

Permethrin Specification

  Permethrin (CAS NO.52645-53-1), its Synonyms are Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester ; Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)- ; Permethrin ; m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate ; Permethrinfog ; Anomethrin N . It is crystalline solid.

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