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右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯

allethrin

CAS: 584-79-2

Molecular Formula: C19H26O3

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  5. 右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯

右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯 - Names and Identifiers

Name allethrin
Synonyms Pynamin
allethrin
Pallethrin
D-allethrin
bioallethrin
(R,S)-3-ally-2-methyl-4-oxo-cyclopent-2-enyl-(1R)-chrysanthemate
(+-)-3-allyl-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(2-methylpropen-1-yl)cyclopropanecarboxylate
2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
(1R)-2-methyl-4-oxo-3-prop-2-en-1-ylcyclopent-2-en-1-yl (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
(1R)-2-methyl-4-oxo-3-prop-2-en-1-ylcyclopent-2-en-1-yl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
(1S)-2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
CAS 584-79-2
EINECS 209-542-4
InChI InChI=1/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3/t14-,16+,17+/m0/s1

右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯 - Physico-chemical Properties

Molecular FormulaC19H26O3
Molar Mass302.41
Density1.05g/cm3
Melting Pointapproximate 4℃
Boling Point386.8°C at 760 mmHg
Flash Point166°C
Water Solubility2 mg l-1
Vapor Presure3.46E-06mmHg at 25°C
AppearanceMorphological Viscous Liquid
ColorClear amber
BRN2294836
Storage Condition2-8°C
Refractive Index1.515
Physical and Chemical Properties

Pale yellow oil used as an insecticide in sprays and dusts. Main mode of entry through skin or by inhalation of dusts or sprays.

UseMainly used for indoor Mosquito and Fly control

右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯 - Risk and Safety

Hazard SymbolsXn - Harmful
Harmful
N - Dangerous for the environment
Dangerous for the environment
Risk CodesR20/22 - Harmful by inhalation and if swallowed.
R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
Safety DescriptionS36 - Wear suitable protective clothing.
S60 - This material and its container must be disposed of as hazardous waste.
S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. 
UN IDsUN 3082
WGK Germany3
RTECSGZ1925000
HS Code29183000
Hazard Class6.1(b)
Packing GroupIII
ToxicityLD50 oral in rabbit: 4290mg/kg

右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯 - Upstream Downstream Industry

Raw MaterialsChloral
Cyclopentanone
2-Methylfuran
Ethyl chrysanthemumate
3-Furaldehyde
Chrysanthemoyl chloride
TRANS-(+)-CHRYSANTHEMIC ACID
rich_d_transallethrin
Conversion catalyst
D-trans-Allethrin

右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯 - Uses and synthesis methods

Production method

1. preparation of allyl alcohol ketone 5-methyl furfural was prepared from 2-methyl furan by Vickers reaction, and gleria reaction (2 & rarr;3), furfural translocation reaction (3 & rarr;4) and isomerization reaction (4 & rarr;5) A new industrial method for preparing allyl alcohol ketone.

The Grignard reaction adopts a continuous process, which is easier to control the temperature than the batch method, magnesium does not need to be activated, and the production device is also simple. The furfural translocation reaction uses water as a solvent, and the reaction pH value is strictly controlled, and the yield can reach 70%; hydroxy The isomerization of cyclopentanone reacts with aqueous trichloroacetaldehyde, followed by triethylamine treatment (or reacts with alkali in aqueous solution, or reacts with aluminum).

The preparation of dextran-rich trans-chrysanthemum acid uses (±) cis-trans chrysanthemum acid ethyl ester to hydrolyze to obtain the corresponding chrysanthemum acid, and then in the presence of a conversion catalyst, react at 120 ℃ for 2h, and translocation to obtain (±) trans-rich chrysanthemum acid (cis/trans = 10/90), (±) trans chrysanthemum acid (cis/trans = 2/98) was obtained by freezing crystallization at -5 ℃. Use dextrorotatory splitting agent, freeze crystallization at -5 ℃, filter, wash the filtrate with dilute hydrochloric acid, separate the water layer, wash the oil layer to neutral, and distill under reduced pressure to obtain (+)-trans-pyrethroid and (-)-trans-chrysanthemum acid.

Synthesis of dextrorotatory trans-allenthrin (+)-trans-chrysanthemum acid and acyl chlorinating agent (PCl3 or SOCl2) to obtain (+)-trans-chrysanthemum chloride. In the presence of pyridine and toluene, allyl alcohol ketone reacts with (+)-trans-chrysanthemum chloride to form the target product, in which the content of dextrorotatory trans is more than 80%. (-) Anti-chrysanthemum acid is racemized to obtain (±) and chrysanthemum acid.

2. ethyl chrysanthemum acid is used as the starting material, saponification, acidification, acyl chlorination, and then esterification are obtained: the obtained product is a mixture of eight isomers, and the quality index of the original drug is the total isomer content ≥ 90.0%. Raw material consumption quota: ethyl chrysanthemum (95.6%)840kg/t, liquid alkali 630kg/t, phosphorus trichloride 1110kg/t, acrylic ketone 550kg/t.

category

Pesticides

Toxicity classification

Highly toxic

Acute toxicity

oral-rat LD50: 425 mg/kg; Oral-mouse LD50: 330 mg/kg

flammability hazard characteristics

Combustible; combustion produces stimulating smoke

storage and transportation features

Ventilated and dry at low temperature; stored separately from warehouse food ingredients

Fire extinguishing agent

Dry powder, foam, sand

Last Update：2024-04-10 22:29:15

右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯 - Nature

NIST chemical information Bioallethrin(584-79-2)
EPA chemical information Allethrin (584-79-2)
Last Update：2024-04-09 20:52:54

右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯 - Security information

toxic substance data 584-79-2(Hazardous Substances Data)
Last Update：2024-04-09 15:16:20
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View History
右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯
6-PHOSPHOGLUCONIC ACID BARIUM GRADE VI
PHOSPHATE FOR CHEESE 835
(R)-2-氨基-3-羟基-3-甲基丁酸
异亮氨酰-异亮氨酰-甘氨酰-亮氨酰-蛋氨酸
2-氨基蒽 标准品
3-羟基-5-羰基-1-环戊烯-1-庚酸甲酯
Raw Materials for 右旋-顺,反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(R,S)-2-甲基-3-烯丙基-4-氧代-环戊-2-烯基酯
Chloral
2-Methylfuran
Chrysanthemoyl chloride
TRANS-(+)-CHRYSANTHEMIC ACID
rich_d_transallethrin
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