(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

C21H20Cl2O3

CAS52645-53-1
GHS07 Gefahrensymbol: Gesundheitsschädlich/Reizend – Ausrufezeichen
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
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Identification

CAS Number
52645-53-1
EC Number
258-067-9
UN Number
3077
Index Number
613-058-00-2
PubChem CID
40326

Physical-chemical properties

Molecular Formula
C21H20Cl2O3
Molar Mass
391.30 g/mol
IUPAC Name
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Chemical Identifiers

InChI
InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3
InChI Key
RLLPVAHGXHCWKJ-UHFFFAOYSA-N

Overview

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate (CAS 52645-53-1) is a synthetic pyrethroid ester with insecticidal properties and complex cyclopropane structure. This chlorinated organic compound, commonly known as permethrin, represents a significant advancement in synthetic pyrethroid chemistry. With its molecular formula C21H20Cl2O3 and molecular weight of 391.3 g/mol, this substance exhibits the characteristic structure of pyrethroid insecticides, featuring a cyclopropane carboxylate core linked to a phenoxybenzyl alcohol moiety. The presence of the 2,2-dichloroethenyl group enhances its biological activity and environmental stability compared to natural pyrethrins. The compound displays moderate acute toxicity (Acute Tox. 4) and acts as a skin sensitizer (Skin Sens. 1), requiring careful handling protocols. Its significant aquatic toxicity (Aquatic Acute 1; Aquatic Chronic 1) necessitates strict environmental controls during use and disposal. The substance is classified under ADR Class 9 for transportation purposes and carries GHS07 and GHS09 pictograms with a "Warning" signal word. Industrial applications include formulation of professional pest control products, agricultural crop protection solutions, and specialized vector control treatments. The compound's efficacy against a broad spectrum of insects makes it valuable in integrated pest management systems. Unlike simpler compounds such as 2-methylpropyl 2-(oxiran-2-yl)acetate, this pyrethroid offers enhanced photostability and residual activity. Manufacturing processes often incorporate stabilizers like triphenyl phosphite to prevent degradation during storage and formulation. The compound's selectivity for insect sodium channels over mammalian targets contributes to its favorable toxicological profile for intended applications. OYSI provides this specialized pyrethroid compound to qualified industrial customers throughout Europe, supporting diverse pest management and agricultural applications.

Safety & Classification

Warning
Classification:

Acute Tox. 4 *; Acute Tox. 4 *; Skin Sens. 1; Aquatic Acute 1; Aquatic Chronic 1

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H332

Harmful if inhaled.

H302

Harmful if swallowed.

H317

May cause an allergic skin reaction.

H400

Very toxic to aquatic life.

H410

Very toxic to aquatic life with long lasting effects.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Inhalation

Harmful

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Skin Contact

Irritant

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Ingestion

Harmful

Measures if substance is accidentally swallowed

First Aid Actions

  • +P301IF SWALLOWED:
  • +P330Rinse mouth.
  • +P331Do NOT induce vomiting.
  • +P310Immediately call a POISON CENTER/doctor.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number3077
ADR Class9
Packing GroupIII
Tunnel Code-
Proper Shipping NamePermethrin (ISO), rein, fest
Marine PollutantNo

Frequently Asked Questions

What is (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is a synthetic pyrethroid insecticide with CAS number 52645-53-1 and molecular formula C21H20Cl2O3. This chemical compound has a molecular weight of 391.3 g/mol and belongs to the cyclopropanecarboxylate class. It is classified as a hazardous substance with acute toxicity and skin sensitization properties, requiring careful handling and environmental protection measures.

What are the physico-chemical properties of (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is typically a solid crystalline substance at room temperature with low water solubility. As a pyrethroid compound, it exhibits good stability under normal storage conditions and is soluble in organic solvents. The presence of chlorine atoms and the cyclopropane ring structure contribute to its chemical stability and biological activity. Specific physical properties may vary depending on purity and crystalline form.

What is (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate used for?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is primarily used as an active ingredient in insecticidal formulations. This pyrethroid compound is effective against various insect pests and is commonly incorporated into agricultural pesticides, household insecticides, and public health applications. It may also serve as an intermediate in the synthesis of other pyrethroid compounds or be used in research and development of pest control products.

How to handle (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate safely?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate requires careful handling due to its Acute Tox. 4 and Skin Sens. 1 classifications. Use appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and protective clothing. Ensure adequate ventilation in work areas and avoid direct skin contact or inhalation. Implement proper hygiene measures and wash hands thoroughly after handling. Follow GHS07 pictogram warnings and maintain emergency procedures.

How to store (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate correctly?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate should be stored in a cool, dry, well-ventilated area away from direct sunlight and heat sources. Keep containers tightly sealed and store away from incompatible materials, oxidizing agents, and strong bases. Due to its environmental hazard classification (GHS09), implement measures to prevent environmental release. Use appropriate secondary containment and ensure storage areas comply with local chemical storage regulations.

What to do in case of contact with (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

Immediate action is required following contact with (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate due to its skin sensitization properties. For skin contact, immediately remove contaminated clothing and wash affected area thoroughly with soap and water. In case of eye contact, rinse immediately with plenty of water for at least 15 minutes. If inhaled, move to fresh air. Seek medical attention if symptoms develop or persist, especially for sensitive individuals.

How to dispose of (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate appropriately?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate must be disposed of as hazardous waste through licensed waste management companies due to its environmental and health hazards. Never dispose of in regular trash, sewers, or environment. Contact authorized hazardous waste disposal services that can handle pesticide-related chemicals. Ensure compliance with local, national, and EU waste disposal regulations. Empty containers may also require special disposal as contaminated packaging.

How to transport (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is classified as ADR Class 9 (Miscellaneous dangerous substances), Packing Group III for transportation purposes. This classification requires specific packaging, labeling, and documentation according to ADR regulations. Use UN-approved packaging and ensure proper hazard labels are applied. Transportation must comply with dangerous goods regulations, and drivers require appropriate ADR training certification for Class 9 substances.

Is (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate subject to specific regulations?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is subject to REACH regulation for chemical registration and evaluation within the EU. It must comply with CLP regulation for classification, labeling, and packaging as indicated by its hazard classifications. The substance is not currently listed as SVHC. Additional regulations may apply including biocidal products regulation if used as active substance in pesticides, and specific national restrictions for pyrethroid compounds.

Where to buy (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in Europe?

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is available through OYSI, a specialized European distributor of technical chemical products. OYSI provides this pyrethroid compound to qualified industrial customers, research institutions, and chemical manufacturers across Europe. As a regulated substance requiring proper handling and documentation, purchases are typically restricted to professional users with appropriate licenses and safety capabilities. Contact OYSI directly for availability, technical specifications, and regulatory compliance support.

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(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is a dangerous good. We support you with labeling, packaging, and transport documentation.

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Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.