Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

C22H19Cl2NO3

trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

CAS67375-30-8
GHS07 Gefahrensymbol: Gesundheitsschädlich/Reizend – Ausrufezeichen
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
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Identification

CAS Number
67375-30-8
EC Number
257-842-9
UN Number
3349
Index Number
607-422-00-X
PubChem CID
93357

Physical-chemical properties

Molecular Formula
C22H19Cl2NO3
Molar Mass
416.30 g/mol
IUPAC Name
trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Chemical Identifiers

InChI
InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1
InChI Key
KAATUXNTWXVJKI-NSHGMRRFSA-N

Overview

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate (CAS 67375-30-8) is a synthetic pyrethroid insecticide with exceptional photostability and broad-spectrum activity. This complex organic compound, with molecular formula C22H19Cl2NO3 and molecular weight 416.3 g/mol, represents a third-generation pyrethroid developed to overcome the photodegradation limitations of earlier synthetic pyrethroids. The molecule features a characteristic cyclopropane carboxylate structure combined with a cyano-substituted benzyl alcohol moiety containing a phenoxyphenyl group, which contributes to its enhanced stability and biological activity. As a member of the pyrethroid family, this compound exhibits neurotoxic properties by disrupting sodium channel function in target organisms, leading to paralysis and death in insects. Unlike simpler chemical structures such as chloromercury compounds, this sophisticated pyrethroid offers selective toxicity with lower mammalian toxicity compared to many conventional insecticides. The substance is classified under multiple hazard categories including Acute Toxicity Category 4, Skin Irritation Category 2, and Skin Sensitization Category 1, requiring careful handling protocols. Its environmental classification as Aquatic Acute 1 and Aquatic Chronic 1 indicates significant aquatic toxicity, necessitating proper containment and disposal procedures. Transportation falls under ADR Class 6.1, reflecting its toxic properties. Primary industrial applications include formulation of agricultural insecticides for crop protection, development of household pest control products, and incorporation into public health vector control programs. The compound's photostability makes it particularly valuable for outdoor applications where UV degradation is a concern. OYSI maintains reliable supply chains for this specialized pyrethroid compound, supporting customers across Europe with consistent quality and regulatory compliance documentation.

Safety & Classification

Warning
Classification:

Acute Tox. 4 *; STOT SE 3; Skin Irrit. 2; Skin Sens. 1; Aquatic Acute 1; Aquatic Chronic 1

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H302

Harmful if swallowed.

H335

May cause respiratory irritation.

H315

Causes skin irritation.

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

Irritant

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 Number3349
ADR Class6.1
Packing GroupIII
Tunnel CodeE
Proper Shipping NameCypermethrin
Marine PollutantNo

Frequently Asked Questions

What is trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is a synthetic pyrethroid insecticide, commonly known as cyhalothrin. This chemical compound has the molecular formula C22H19Cl2NO3 and a molecular weight of 416.3 g/mol. It belongs to the class of cyclopropane carboxylates and is characterized by its complex stereochemical structure with specific R and S configurations that determine its biological activity and effectiveness as a pest control agent.

What are the physicochemical properties of trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is typically a colorless to pale yellow crystalline solid at room temperature. It has low water solubility but is soluble in organic solvents such as acetone, methanol, and toluene. The compound is relatively stable under normal conditions but may decompose under extreme heat or alkaline conditions. Its molecular structure contains chlorine atoms and aromatic rings, contributing to its lipophilic nature and biological activity.

What is trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate used for?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is primarily used as an active ingredient in insecticidal formulations. It serves as a broad-spectrum insecticide for agricultural crop protection, controlling various pests including lepidopteran larvae, aphids, and other harmful insects. The compound is also utilized in professional pest control applications for structural pest management. Its high potency and relatively low application rates make it valuable in integrated pest management programs across different agricultural and horticultural sectors.

How to handle trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate safely?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate requires careful handling with appropriate personal protective equipment. Wear chemical-resistant gloves, safety goggles, and protective clothing to prevent skin and eye contact. Use respiratory protection in poorly ventilated areas to avoid inhalation. Work in well-ventilated spaces and avoid eating, drinking, or smoking during handling. Wash hands thoroughly after use. The substance is classified as Acute Tox. 4, Skin Irrit. 2, and Skin Sens. 1, requiring precautions against dermal exposure and sensitization.

How to store trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate correctly?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-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 closed and protected from moisture to prevent degradation. Store away from incompatible materials such as strong bases, oxidizing agents, and food products. Maintain storage temperatures below 25°C when possible. Ensure storage areas are equipped with appropriate containment measures and are accessible only to authorized personnel. Regular inspection of containers for damage or leaks is recommended.

What to do in case of contact with trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

Immediate action is required upon contact with trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate. For skin contact, remove contaminated clothing and wash affected area thoroughly with soap and water for at least 15 minutes. In case of eye contact, rinse immediately with clean water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air immediately. If swallowed, do not induce vomiting and seek immediate medical attention. Always consult a physician and provide the safety data sheet when seeking medical treatment.

How to dispose of trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate appropriately?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate must be disposed of through authorized hazardous waste disposal facilities. The substance cannot be discharged to sewers, waterways, or regular municipal waste due to its classification as Aquatic Acute 1 and Aquatic Chronic 1. Contact licensed waste management companies for proper collection and treatment. Empty containers should also be handled as hazardous waste. Follow local, national, and EU regulations for hazardous waste disposal. Incineration at high temperatures in approved facilities is typically the preferred disposal method.

How to transport trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is classified under ADR Class 6.1, Packing Group III for transport purposes. It must be shipped as a toxic substance requiring appropriate dangerous goods packaging, labeling, and documentation. Packages must bear proper shipping names, UN numbers, and hazard labels. Transport vehicles require proper placarding and emergency information. Only certified carriers with dangerous goods authorization should handle shipment. Special precautions are needed to prevent release during transport, and emergency response procedures must be readily available.

Is trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate subject to specific regulations?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is subject to comprehensive EU chemical regulations. It falls under REACH regulation requiring registration and compliance with substance identification and safety requirements. CLP classification applies with mandatory hazard labeling showing GHS07 and GHS09 pictograms and 'Warning' signal word. The substance is regulated under biocide and plant protection product legislation. Although not currently listed as SVHC, regulatory status should be monitored regularly as classifications can change based on new scientific evidence.

Where to buy trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in Europe?

Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate is available through OYSI, a specialized European distributor of technical chemicals. OYSI provides this substance to qualified industrial customers with proper handling capabilities and regulatory compliance. As a controlled substance requiring specialized handling, purchases are restricted to authorized users with appropriate licenses and facilities. Contact OYSI directly for availability, technical specifications, and regulatory documentation. All sales comply with European chemical distribution regulations and require proper end-use verification.

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Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-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.