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
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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 potent neurotoxic properties against target pests. This complex organic compound, with molecular formula C22H19Cl2NO3 and molecular weight 416.3 g/mol, represents a sophisticated example of modern pesticide chemistry. The molecule features a characteristic cyclopropane carboxylate structure combined with a cyano-substituted phenoxyphenyl group, conferring its insecticidal activity through sodium channel modulation in insect nervous systems. The stereochemistry is precisely defined with (S), (1R,3R) configurations that are critical for biological activity. From a safety perspective, this substance requires careful handling protocols. It is classified under multiple hazard categories including Acute Toxicity Category 4, Skin Irritation Category 2, and Skin Sensitization Category 1. The compound also presents significant environmental concerns with Aquatic Acute and Chronic toxicity ratings of Category 1, necessitating strict containment measures. Transport regulations classify it under ADR Class 6.1, reflecting its toxic nature. Industrial applications primarily center on agricultural pest control formulations, where it serves as an active ingredient in professional-grade insecticides. The compound is also utilized in public health vector control programs and specialized industrial biocide applications. Unlike simpler chemical structures such as chloromercury compounds, this pyrethroid offers selective toxicity profiles that minimize non-target effects when properly formulated. OYSI maintains reliable supply chains for this specialized compound, supporting European customers with comprehensive technical documentation and regulatory compliance support for their formulation requirements.
Safety & Classification
Acute Tox. 4 *; STOT SE 3; Skin Irrit. 2; Skin Sens. 1; Aquatic Acute 1; Aquatic Chronic 1
GHS Pictograms
HHazard Statements (H-Statements)
Describe the nature and severity of the hazard
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
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
Measures if substance contacts the skin
Ingestion
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 Number | 3349 |
| ADR Class | 6.1 |
| Packing Group | III |
| Tunnel Code | E |
| Proper Shipping Name | Cypermethrin |
| Marine Pollutant | No |
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 with the molecular formula C22H19Cl2NO3 and CAS number 67375-30-8. This compound has a molecular weight of 416.3 g/mol and belongs to the cyclopropane carboxylate family of pesticides, characterized by its complex stereochemical structure containing phenoxy and cyano functional groups.
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 crystalline solid at room temperature with low water solubility. The compound exhibits stability under normal conditions but may decompose under extreme heat or UV exposure. Its lipophilic nature allows good penetration through biological membranes, which is essential for its pesticidal activity. The presence of chlorine atoms and aromatic rings contributes to its persistence and bioactivity.
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 for agricultural and pest control applications. It serves as a broad-spectrum insecticide effective against various flying and crawling insects. The compound is incorporated into professional pest control products, agricultural sprays, and household insecticides due to its potent neurotoxic effects on target insects while maintaining relatively lower mammalian toxicity.
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 including chemical-resistant gloves, safety goggles, and protective clothing. Work in well-ventilated areas to minimize inhalation exposure. Avoid skin and eye contact due to its irritant properties and potential for sensitization. Use proper handling techniques to prevent spills and ensure immediate cleanup of any accidental releases to protect the aquatic environment.
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 sealed and store separately from food, feed, and incompatible materials. Due to its aquatic toxicity classification, ensure storage areas have appropriate containment measures to prevent environmental contamination. Maintain storage temperature below 25°C and protect from moisture to preserve product stability and prevent degradation.
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?
In case of skin contact with trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate, immediately remove contaminated clothing and wash the affected area thoroughly with soap and water. For eye contact, rinse immediately with plenty of clean water for at least 15 minutes. If inhaled, move to fresh air immediately. Seek medical attention if symptoms persist or worsen, especially given the compound's acute toxicity classification. Do not induce vomiting if ingested and contact poison control immediately.
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 licensed hazardous waste disposal facilities due to its toxic and environmentally hazardous properties. Never dispose of this substance in regular waste streams, sewers, or waterways given its acute and chronic aquatic toxicity. Contaminated packaging should also be treated as hazardous waste. Consult local environmental authorities for specific disposal requirements and approved waste management contractors in your region.
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 as ADR Class 6.1 (Toxic substances), Packing Group III for transportation purposes. Packages must be properly labeled with appropriate hazard labels and shipping names. Transport vehicles should be equipped with appropriate safety equipment and drivers must have proper training for toxic substance transport. Ensure packages are secured to prevent damage during transit and have emergency response information 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 REACH regulation for chemical registration and CLP regulation for classification and labeling in the European Union. The substance is not currently listed as an SVHC (Substance of Very High Concern). As a pesticide active ingredient, it may also be subject to biocidal product regulations and plant protection product legislation, requiring specific authorizations for commercial use in pest control formulations.
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 and pharmaceutical intermediates. OYSI provides this compound to qualified industrial customers, research institutions, and pesticide manufacturers across Europe. Due to its toxic properties and regulatory requirements, purchase is typically restricted to licensed professionals in the pest control, agricultural, or chemical manufacturing industries who can demonstrate proper handling capabilities and intended use compliance.
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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.
Data Sources
Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.