Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
C22H19Br2NO3
trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
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Identification
- CAS Number
- 52918-63-5
- EC Number
- 258-256-6
- UN Number
- 3349
- Index Number
- 607-319-00-X
- PubChem CID
- 40585
Physical-chemical properties
- Molecular Formula
- C22H19Br2NO3
- Molar Mass
- 505.20 g/mol
- IUPAC Name
- trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Chemical Identifiers
- InChI
- InChI=1S/C22H19Br2NO3/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
- OWZREIFADZCYQD-NSHGMRRFSA-N
Overview
trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate (CAS 52918-63-5) is a synthetic pyrethroid insecticide with high toxicity and aquatic environmental hazards. This complex organobrominated compound belongs to the pyrethroid family of synthetic insecticides, characterized by its distinctive cyclopropane carboxylate structure combined with a phenoxyphenyl moiety. The presence of two bromine atoms in the dibromoethenyl group significantly influences its biological activity and environmental persistence. With a molecular formula of C22H19Br2NO3 and molecular weight of 505.2 g/mol, this substance exhibits the stereochemical complexity typical of advanced pyrethroid formulations. The compound presents significant safety considerations, classified under GHS pictograms GHS06 and GHS09, indicating both acute toxicity and environmental hazards. Its Acute Tox. 3 classification for multiple exposure routes, combined with Aquatic Acute 1 and Aquatic Chronic 1 classifications, necessitates careful handling protocols and environmental protection measures. The ADR Class 6.1 designation requires specialized transport procedures for toxic substances. Industrial applications primarily focus on professional pest control formulations where high efficacy against resistant insect populations is required. The compound's stereochemical configuration provides enhanced selectivity compared to simpler carbamate derivatives like [4-(dimethylamino)-3-methylphenyl] N-methylcarbamate. Unlike organophosphate alternatives such as diethoxy-[(5-phenyl-1,2-oxazol-3-yl)oxy]-sulfanylidene-lambda5-phosphane, this pyrethroid offers different modes of action valuable in integrated pest management strategies. OYSI maintains reliable supply chains for this specialized active ingredient, supporting European manufacturers in the agrochemical and professional pest control sectors with consistent quality and regulatory compliance.
Safety & Classification
Acute Tox. 3 *; Acute Tox. 3 *; 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:
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 | II |
| Tunnel Code | D/E |
| Proper Shipping Name | Deltamethrin (ISO) |
| Marine Pollutant | No |
Frequently Asked Questions
What is trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate is a synthetic pyrethroid insecticide commonly known as deltamethrin. This chemical compound has the molecular formula C22H19Br2NO3 and a molecular weight of 505.2 g/mol. It belongs to the class of highly effective insecticides used for pest control applications. The substance is characterized by its complex stereochemical structure containing bromine atoms and a cyclopropane ring system.
What are the physicochemical properties of trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate typically appears as a white to beige crystalline solid at room temperature. The compound has low water solubility but is soluble in organic solvents such as acetone, methanol, and xylene. It exhibits thermal stability under normal conditions and has a relatively high molecular weight of 505.2 g/mol due to its complex organic structure containing bromine substituents.
What is trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate used for?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate is primarily used as an active ingredient in insecticidal formulations for agricultural and public health applications. It serves as a broad-spectrum insecticide for crop protection against various pests including lepidoptera, coleoptera, and diptera. The compound is also utilized in vector control programs for disease prevention and in professional pest management services for both indoor and outdoor applications.
How to handle trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate safely?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate requires careful handling due to its Acute Tox. 3 classification. Always wear appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and respiratory protection when handling. Work in well-ventilated areas or under fume extraction systems. Avoid direct skin contact, inhalation, and ingestion. Wash hands thoroughly after handling and remove contaminated clothing immediately to prevent prolonged exposure.
How to store trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate correctly?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-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 in original packaging. Due to its aquatic toxicity classification, ensure storage areas have appropriate containment measures to prevent environmental release. Store away from incompatible materials such as strong oxidizers and bases. Maintain storage temperature below 30°C for optimal stability.
What to do in case of contact with trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate?
In case of skin contact with trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate, immediately remove contaminated clothing and wash affected area thoroughly with soap and water for at least 15 minutes. If inhaled, move to fresh air immediately. For eye contact, rinse with clean water for 15 minutes. If ingested, do not induce vomiting and seek immediate medical attention. Always consult a physician and provide the safety data sheet for proper medical treatment.
How to dispose of trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate appropriately?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate must be disposed of as hazardous waste through licensed waste management companies due to its acute toxicity and environmental hazard classifications. Never dispose of in regular waste streams or pour down drains. The substance requires specialized treatment methods such as high-temperature incineration under controlled conditions. Always comply with local and national waste disposal regulations and obtain proper waste disposal documentation.
How to transport trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate is classified under ADR Class 6.1 (toxic substances) Packing Group II, indicating moderate danger during transport. The substance requires appropriate UN specification packaging and hazard labeling including GHS06 and GHS09 pictograms. Transport must comply with dangerous goods regulations, including proper documentation, driver training, and emergency response procedures. Vehicles must carry appropriate emergency equipment and placarding for Class 6.1 materials.
Is trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate subject to specific regulations?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate is subject to comprehensive chemical regulations including REACH registration requirements for manufacturing and import in the European Union. The substance must comply with CLP regulation for classification and labeling as indicated by its Acute Tox. 3 and aquatic hazard classifications. While not currently listed as an SVHC, it may be subject to biocide regulations and plant protection product authorization depending on intended use.
Where to buy trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate in Europe?
Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-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 appropriate handling capabilities and regulatory compliance. As a controlled chemical substance, purchase typically requires demonstration of legitimate use, proper storage facilities, and compliance with relevant safety and environmental regulations. Contact OYSI directly for availability, specifications, and regulatory documentation requirements for your specific application.
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Trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-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.