ChemicalBook--->CAS DataBase List--->54406-48-3

54406-48-3

54406-48-3 Structure

54406-48-3 Structure
IdentificationMore
[Name]

Empenthrin
[CAS]

54406-48-3
[Synonyms]

1-ETHINYL-2-METHYL-2-PENTEN-1-YL CHRYSANTHEMATE
D-EMPENTHRIN
[(E)-4-methylhept-4-en-1-yn-3-yl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
EMPENTHRIN
VAPORTHRIN
(rs)-(e)-1-ethynyl-2-methyl-2-pentenyl(1r)-cis,trans-chrysanthemate
2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylicaci1-ethynyl-2
2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylicaci1-ethynyl-2-methyl-2-pentenylester
Cyclopropanecarboxylicacid,2,2-dimethyl-3-(2-methyl-1-propenyl)-,1-ethynyl-2-methyl-2-pentenylester
empenthrin[(1r)isomers]
ma108
-methyl-2-pentenylester
s2852
s2852f
s2852forte
1-ethynyl-2-methylpent-2-enyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
Empenthrin, Pestanal
(E)-1-Ethynyl-2-methylpenten-2-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Chrysanthemic acid, (E)-1-ethynyl-2-methylpenten-2-yl ester
empenthrin (bsi, draft e-iso)
[EINECS(EC#)]

259-154-4
[Molecular Formula]

C18H25O2-
[MDL Number]

MFCD01745518
[Molecular Weight]

273.39
[MOL File]

54406-48-3.mol
Chemical PropertiesBack Directory
[Appearance]

liquid
[Melting point ]

25°C
[Boiling point ]

377.38°C (rough estimate)
[density ]

0.9965 (rough estimate)
[vapor pressure ]

1.4×10-2 Pa (23.6 °C)
[refractive index ]

1.5510 (estimate)
[storage temp. ]

2-8°C
[Water Solubility ]

0.11 mg l-1 (25 °C)
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Henry's Law Constant]

2.9×10-2 mol/(m3Pa) at 25℃, Ebert et al. (2023)
[CAS DataBase Reference]

54406-48-3(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn;N,N,Xn
[Risk Statements ]

R22:Harmful if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
[Safety Statements ]

S61:Avoid release to the environment. Refer to special instructions safety data sheet .
[RIDADR ]

UN 3082
[RTECS ]

GZ1728000
[HS Code ]

29162090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ammonium chloride-->Lithium-->Acetylene-->Permethric acid-->Chrysanthemoyl chloride-->1-ethynyl-2-methyl penten-2-ol-->2-Methyl-1-pentene-->4-Hepten-1-yn-3-ol, 4-methyl- -->2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid
Hazard InformationBack Directory
[Description]

Empenthrin, also known as vaporthrin, (2E)-1-ethynyl-2-methyl-2-penten-1-yl 2,2- dimethyl-3-(2-methyl-1-propen-1-yl) cyclopropanecarboxylate, is a derivative of 1-ethynyl- 2-methyl penten-2-ol. The vapor pressure of empenthrin at room temperature is suitable and therefore it has a natural volatility. At 30 °C, the vapor pressures of empenthrin and allethrin are 1.62×103 and 1.20×104 mmHg, respectively. Thus, the vapor pressure of empenthrin is about 10 times more than that of allethrin. Moreover, empenthrin is odorless. It has strong killing activity and repellent effect on pests and is very suitable for textile mothproofing.
[Chemical Properties]

liquid
[Uses]

Empenthrin is an insecticidal pyrethroid compound.
[Uses]

Empenthrin is used as a domestic insecticide, especially against moths and other insects which attack fabrics.
[Definition]

ChEBI:Empenthrin is a monoterpenoid.
[Preparation]

About 3.72 g (0.03 mol) of 2-methyl-1-ethynyl-2-pentenol and 3.16 g (0.04 mol) of pyridine were added to toluene to form a solution. A toluene solution containing 5.6 g (0.03 mol) of Chrysanthemoyl chloride was added in a dropwise manner. The reaction was carried out at a temperature of 40–50°C for 6h. After reaction, the reaction solution was washed with water until neutral, dried and then subjected to distillation under reduced pressure. About 5.7 g of empenthrin was collected from a fraction of 120–126°C (0.03 mmHg). The yield of empenthrin was 69%.
[Mechanism of action]

Contact action. Sodium channel modulator.
[Metabolic pathway]

Empenthrin is a low molecular weight ester of (1R)-chrysanthemic acid (2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid). It has a relatively high vapour pressure and, unlike most pyrethroids, it is effective against flying insects. The molecule has three chiral centres and geometric isomerism in the alcohol group but, with the exception of the 1R acid, the full isomer mixture is used. As the insecticide has been developed for domestic use, it is unlikely that there will be a requirement for metabolism studies in plants or for extensive environmental fate studies. Its metabolism in rats has been reported, with particular attention paid to the fate of the novel alcohol moiety. As with other pyrethroids, ester cleavage and oxidation and conjugation of the alcohol metabolite predominated. The fate of the chrysanthemic acids can be assessed by reference to phenothrin.
[Degradation]

Empenthrin is a stable molecule but it would be expected to be labile at pH values above 10.
[Pesticide Type]

Insecticide
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

54406-48-3(sigmaaldrich)
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