(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

(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 - 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

(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 - Physico-chemical Properties

Molecular Formula	C19H26O3
Molar Mass	302.41
Density	1.05g/cm³
Melting Point	approximate 4℃
Boling Point	386.8°C at 760 mmHg
Flash Point	166°C
Water Solubility	2 mg l-1
Vapor Presure	3.46E-06mmHg at 25°C
Appearance	Morphological Viscous Liquid
Color	Clear amber
BRN	2294836
Storage Condition	2-8°C
Refractive Index	1.515
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.
Use	Mainly used for indoor Mosquito and Fly control

(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 - Risk and Safety

Hazard Symbols	Xn - Harmful N - Dangerous for the environment
Risk Codes	R20/22 - Harmful by inhalation and if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Description	S36 - 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 IDs	UN 3082
WGK Germany	3
RTECS	GZ1925000
HS Code	29183000
Hazard Class	6.1(b)
Packing Group	III
Toxicity	LD50 oral in rabbit: 4290mg/kg

(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 - Upstream Downstream Industry

Raw Materials

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

(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 - 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

(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 - Nature

NIST chemical information	Bioallethrin(584-79-2)
EPA chemical information	Allethrin (584-79-2)

Last Update：2024-04-09 20:52:54

(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 - Security information

toxic substance data

584-79-2(Hazardous Substances Data)

Last Update：2024-04-09 15:16:20

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Product Name: Allethrin Request for quotation
CAS: 584-79-2
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
QQ: 2470479589

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Hefei TNJ Chemical Industry Co.,Ltd.

Product Name: allethrin Request for quotation
CAS: 584-79-2
Tel: 0086-551-65418684
Email: sales@tnjchem.com
　　　　 info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840

Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog

Shanghai Yuanye Bio-Technology Co., Ltd.

Multiple Specifications

Product Name: Bioallethrin Visit Supplier Webpage Request for quotation
CAS: 584-79-2
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View History

(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

Raw Materials for (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

Chloral
Cyclopentanone
Ethyl chrysanthemumate
3-Furaldehyde
TRANS-(+)-CHRYSANTHEMIC ACID
rich_d_transallethrin

(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

allethrin

CAS: 584-79-2

Molecular Formula: C19H26O3

(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 - Names and Identifiers

(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 - Physico-chemical Properties

(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 - Risk and Safety

(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 - Upstream Downstream Industry

(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 - Uses and synthesis methods

(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 - Nature

(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 - Security information

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(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 Request for Quotation

allethrin

CAS: 584-79-2

Molecular Formula: C19H26O3

(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 - Names and Identifiers

(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 - Physico-chemical Properties

(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 - Risk and Safety

(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 - Upstream Downstream Industry

(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 - Uses and synthesis methods

(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 - Nature

(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 - Security information

Supplier List

(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