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

CAS52918-63-5
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
Danger

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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 acute toxicity and significant environmental persistence. This complex organobrominated compound belongs to the pyrethroid family of synthetic insecticides, characterized by its distinctive cyclopropane carboxylate structure combined with a phenoxyphenyl moiety. With a molecular formula of C22H19Br2NO3 and molecular weight of 505.2 g/mol, this substance represents an advanced synthetic approach to pest control chemistry. The presence of two bromine atoms in the dibromoethenyl group contributes to its enhanced stability and biological activity compared to simpler pyrethroid structures. The compound exhibits significant safety concerns, classified under acute toxicity category 3 with both GHS06 and GHS09 pictograms indicating acute toxicity and environmental hazards respectively. Its classification as Aquatic Acute 1 and Aquatic Chronic 1 reflects severe toxicity to aquatic organisms with long-lasting effects. Transportation falls under ADR class 6.1, requiring appropriate hazardous material handling protocols. These safety characteristics distinguish it from related compounds such as diethoxy-[(5-phenyl-1,2-oxazol-3-yl)oxy]-sulfanylidene-lambda5-phosphane, which typically presents different toxicity profiles. Primary industrial applications include agricultural pest control formulations, particularly for crops requiring persistent insecticidal protection, professional pest management solutions for structural applications, and specialized vector control programs where extended efficacy is essential. The compound's stereochemical configuration contributes to its selective biological activity. OYSI maintains reliable supply chains for this technical-grade pyrethroid, supporting European customers with comprehensive documentation and regulatory compliance assistance.

Safety & Classification

Danger
Classification:

Acute Tox. 3 *; Acute Tox. 3 *; Aquatic Acute 1; Aquatic Chronic 1

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H331

Toxic if inhaled.

H301

Toxic if swallowed.

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

Toxic

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

Toxic

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 GroupII
Tunnel CodeD/E
Proper Shipping NameDeltamethrin (ISO)
Marine PollutantNo

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 features a complex molecular structure with the formula C22H19Br2NO3 and a molecular weight of 505.2 g/mol. It belongs to the class of pyrethroid pesticides and is characterized by its high insecticidal activity and environmental persistence. The substance is classified as toxic and hazardous to aquatic environments.

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 poor water solubility but dissolves readily in organic solvents such as acetone, methanol, and xylene. It exhibits stability under normal conditions but may decompose when exposed to strong alkali or high temperatures. The substance has a molecular weight of 505.2 g/mol and contains two bromine atoms in its structure.

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 insecticide formulations for agricultural and public health applications. It effectively controls a wide range of insects including lepidoptera, coleoptera, and diptera. The substance is commonly incorporated into crop protection products, household insecticides, and vector control programs. Its high potency allows for low application rates while maintaining excellent efficacy against target pests.

How to safely handle 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 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. Work in well-ventilated areas or under fume extraction systems. Avoid direct skin contact, inhalation, and ingestion. Wash hands thoroughly after handling and before eating or drinking. Keep away from heat sources and incompatible materials.

How to properly store 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 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 chemicals such as strong acids and bases. Maintain storage temperatures below 25°C to prevent degradation. Use appropriate containment measures to prevent environmental release. Ensure storage areas comply with local regulations for toxic substances and have appropriate emergency response equipment available.

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?

Immediate first aid is essential following contact with trans-[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate. For skin contact, remove contaminated clothing and wash affected area thoroughly with soap and water. In case of eye contact, rinse immediately with plenty of clean water for at least 15 minutes. If ingested, do not induce vomiting and seek immediate medical attention. For inhalation, move to fresh air immediately. Contact emergency services and provide the safety data sheet to medical personnel.

How to properly dispose 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 must be disposed of as hazardous waste through licensed waste disposal companies. Never dispose of this substance in regular trash, sewage systems, or soil due to its aquatic toxicity classification. Incineration at high temperatures in approved facilities is the preferred disposal method. Empty containers should be triple-rinsed and disposed of according to local regulations. Consult local environmental authorities for specific disposal requirements and approved waste management facilities in your area.

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. Transportation requires appropriate UN-approved packaging, proper labeling with GHS06 and GHS09 pictograms, and accompanying transport documentation. Vehicles must carry emergency equipment and drivers need hazardous goods certification. Ensure packages are secured against movement and damage during transport. Follow specific routing restrictions and emergency response procedures as required by dangerous goods regulations.

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 extensive regulatory oversight under REACH and CLP regulations in Europe. While not currently listed as an SVHC, it requires registration for commercial use and must be classified and labeled according to its hazard profile. The substance is regulated under pesticide legislation and may have restrictions on use in certain applications. Companies handling this chemical must comply with occupational safety regulations and environmental protection requirements including proper risk assessment and exposure controls.

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 chemical products. OYSI provides this substance to qualified industrial customers with appropriate handling capabilities and regulatory compliance. As a controlled chemical requiring specialized handling, purchase is typically restricted to licensed companies in pesticide manufacturing, research institutions, and authorized industrial users. Contact OYSI directly to discuss availability, technical specifications, and regulatory requirements for your specific application needs.

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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.

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Data Sources

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