[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate

C25H22ClNO3

CAS66230-04-4
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS08 Gefahrensymbol: Gesundheitsgefahr – Gesundheitsgefahr
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
Danger

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Identification

CAS Number
66230-04-4
UN Number
3349
Index Number
608-058-00-4
PubChem CID
10342051

Physical-chemical properties

Molecular Formula
C25H22ClNO3
Molar Mass
419.90 g/mol
IUPAC Name
[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate

Chemical Identifiers

InChI
InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m1/s1
InChI Key
NYPJDWWKZLNGGM-RPWUZVMVSA-N

Overview

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate (CAS 66230-04-4) is a synthetic pyrethroid ester compound with insecticidal properties and significant environmental toxicity concerns. This chiral organochlorine compound, with molecular formula C25H22ClNO3 and molecular weight 419.9 g/mol, belongs to the pyrethroid family of synthetic insecticides. The molecule features a complex stereochemical structure containing both cyano and phenoxy functional groups, along with a chlorinated aromatic ring system that contributes to its biological activity. The presence of two chiral centers (S-configuration) is critical for its pesticidal efficacy, distinguishing it from other structural isomers. The compound presents significant safety considerations, classified under multiple hazard categories including acute toxicity (Acute Tox. 3), specific target organ toxicity (STOT SE 1, STOT RE 2), skin sensitization (Skin Sens. 1), and severe aquatic toxicity (Aquatic Acute 1, Aquatic Chronic 1). These classifications necessitate careful handling protocols and appropriate personal protective equipment during industrial use. The ADR Class 6.1 designation indicates its classification as a toxic substance for transportation purposes, requiring specialized logistics and documentation. Primary industrial applications include formulation into agricultural pesticides for crop protection, development of household insecticide products, and incorporation into professional pest control solutions. Unlike simpler aromatic compounds such as N-methylaniline, this pyrethroid exhibits high selectivity for insect nervous systems while maintaining relatively lower mammalian toxicity at controlled exposure levels. OYSI provides this technical-grade pyrethroid compound to qualified industrial customers across Europe, supporting applications in agricultural chemical manufacturing and specialized pest control product development.

Safety & Classification

Danger
Classification:

Acute Tox. 3; Acute Tox. 3; STOT SE 1; STOT RE 2; Skin Sens. 1; 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.

H370

Causes damage to organs.

H373

May cause damage to organs through prolonged or repeated exposure.

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

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:

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

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 GroupIII
Tunnel CodeE
Proper Shipping NameEsfenvalerat (ISO)
Marine PollutantNo

Frequently Asked Questions

What is [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate is a synthetic pyrethroid insecticide with the molecular formula C25H22ClNO3 and CAS number 66230-04-4. This complex organic compound has a molecular weight of 419.9 g/mol and belongs to the pyrethroid family of pesticides. It is characterized by its stereochemical configuration with two chiral centers in the (S) and (2S) positions, which are crucial for its biological activity and effectiveness as an insecticidal agent.

What are the physicochemical properties of [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate is typically a crystalline solid at room temperature with a molecular weight of 419.9 g/mol. As a pyrethroid compound, it generally exhibits low water solubility but good solubility in organic solvents such as acetone, methanol, and dichloromethane. The compound is relatively stable under normal conditions but may degrade under extreme pH conditions or prolonged exposure to UV light, which is characteristic of most pyrethroid insecticides.

What is [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate used for?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate is primarily used as an active ingredient in insecticidal formulations for agricultural and professional pest control applications. This pyrethroid compound is effective against a broad spectrum of insects including lepidoptera, coleoptera, and diptera species. It is commonly incorporated into crop protection products, public health pesticides, and professional pest management solutions due to its potent neurotoxic effects on target insects while maintaining relatively lower mammalian toxicity compared to older insecticide classes.

How to handle [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate safely?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate requires careful handling due to its Acute Tox. 3 classification and skin sensitization potential. Essential personal protective equipment includes chemical-resistant gloves, safety goggles, and respiratory protection when handling powders or during mixing operations. Work should be conducted in well-ventilated areas or under fume extraction systems. Avoid skin and eye contact, and prevent inhalation of dust or vapors. Given its aquatic toxicity classification, prevent environmental release and ensure proper containment during handling operations.

How to store [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate correctly?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate should be stored in a cool, dry, well-ventilated area away from direct sunlight and heat sources. The storage area must be secured and accessible only to authorized personnel due to its toxic properties. Keep containers tightly sealed in original packaging to prevent moisture absorption and contamination. Store away from incompatible materials such as strong bases, oxidizing agents, and food products. Given its aquatic toxicity, ensure storage areas have appropriate spill containment measures and are located away from water sources.

What to do in case of contact with [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate?

Immediate first aid measures for [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate exposure include: For skin contact, remove contaminated clothing and wash affected area thoroughly with soap and water for at least 15 minutes. For eye contact, rinse immediately with clean water for at least 15 minutes and remove contact lenses if present. If inhaled, move to fresh air immediately. If swallowed, do not induce vomiting and seek immediate medical attention. Always seek professional medical advice and provide the safety data sheet to medical personnel, especially given the compound's neurotoxic potential.

How to dispose of [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate properly?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate must be disposed of as hazardous waste according to local, national, and EU regulations. Due to its classification as Acute Tox. 3 and aquatic toxicity, it requires specialized treatment at licensed hazardous waste facilities. High-temperature incineration is typically the preferred disposal method for pyrethroid compounds. Empty containers should also be treated as hazardous waste. Never dispose of this substance through regular waste streams, sewage systems, or allow environmental release due to its persistence and aquatic toxicity.

How to transport [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate is classified as ADR Class 6.1 (toxic substances), Packing Group III for transport purposes. Packages must bear appropriate hazard labels including the toxic symbol and proper shipping name. Transportation requires compliance with ADR regulations including proper packaging, documentation, and driver certification for dangerous goods. Vehicles must carry appropriate emergency equipment and spill response materials. The compound must be segregated from food products, animal feed, and incompatible substances during transport to prevent cross-contamination and ensure safety.

Is [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate subject to specific regulations?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate is subject to multiple European regulations including REACH registration requirements, CLP classification and labeling, and the Biocidal Products Regulation (BPR) when used in biocidal applications. While not currently listed as a SVHC substance, its Acute Tox. 3 and environmental classifications require compliance with strict handling, storage, and disposal regulations. The compound may also be subject to national pesticide registration requirements and workplace exposure limits. Users must ensure proper risk assessments and safety measures are implemented according to regulatory guidelines.

Where to buy [(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate in Europe?

[(S)-cyano-(3-phenoxyphenyl)methyl] (2S)-2-(4-chlorophenyl)-3-methylbutanoate is available through OYSI, a specialized European distributor of chemical products. OYSI provides this pyrethroid compound to qualified industrial and professional customers across Europe, ensuring full regulatory compliance and proper documentation. As a restricted chemical due to its toxicological profile, purchase requires appropriate business credentials and intended use declarations. OYSI maintains inventory to support customer requirements while ensuring proper handling, storage, and transportation according to ADR Class 6.1 regulations and European chemical safety standards.

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Data Sources

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