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Usage

Uses

Used in Household Insecticide Products:
Transfluthrin is used as an active ingredient in various household insecticide products such as mosquito coils, mats, and liquid vaporizers. It provides effective control of pests, ensuring a comfortable living environment.
Used in Public Health Vector Control Programs:
In public health vector control programs, transfluthrin is used as an insecticide and acaricide to control disease-carrying insects like mosquitoes. Its effectiveness in controlling these pests helps in reducing the spread of vector-borne diseases, thus contributing to improved public health.
It is important to use transfluthrin with caution and follow the recommended safety guidelines to minimize potential risks to human health and the environment.

InChI:InChI=1/C10H14Cl2O2/c1-4-14-9(13)8-6(5-7(11)12)10(8,2)3/h5-6,8H,4H2,1-3H3/t6-,8-/m0/s1

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 66692-75-9 ethyl 3-formyl-2,2-dimethylcyclopropanecarboxylate 
• 1608-26-0 Hexamethylphosphorous triamide 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 865-47-4 potassium tert-butylate 
• 650-51-1 sodium trichloroacetate 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 59609-50-6 ethyl 2-(2,2-dichlorovinyl)-3,3-dimethyl-1-ethoxycarbonylcyclopropanecarboxylate 
• 67-68-5 dimethyl sulfoxide 
• 65771-92-8 3-methyl-3-chloro-2-(2',2'-dichlorovinyl)-butanecarboxylic acid ethyl ester 
• 2304-30-5 tetra-n-butylphosphonium chloride 
• 63142-56-3 ethyl (+/-)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 

Downstream Products

• 55701-08-1 (-)-cis-(1S,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarboxylic acid 
• 78548-58-0 (1S,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid ethyl ester 
• 55667-40-8 1(R)-cis-permethrinic acid 
• 569679-06-7 3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate 

Relevant academic research and scientific papers

A diastereoselective synthesis of boceprevir's gem-dimethyl bicyclic [3.1.0] proline intermediate from an insecticide ingredient cis-cypermethric acid

An efficient multi-gram synthesis of (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate, a key chiral bicyclic proline fragment employed in the construction of the potent anti-HCV drug boceprevir, has been presented. The synthetic route commences with the readily available cis-cypermethric acid, a cheap source of the cyclopropane ring required in the targeted compound, and utilizes the cis-orientation of the 2,2-dichlorovinyl and carboxylic acid side arms, already present in the starting material, to effect a diastereoselective construction of the proline moiety.

A Practical and Efficient Synthesis of Fluorinated Pyrethroids. cis-3-(2-Chloro--3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates

A practical and efficient route to fluorinated pyrethroids has been developed which involves the selective formation of the cis-cyclopropane ring using intramolecular alkylation of the haloaldehyde and a novel transformation of the aldehydes to the corresponding esters via the cyanohydrins.

Reductive Addition of Polyhalomethanes and Their Related Compounds to Aldehydes and 1,2-Elimination of the Coupling Products in a Pb/Al Bimetal Redox System

A Pb/Al bimetal system was used to carry out reductive addition of tetrachloromethane, tetrabromomethane, bromotrichloromethane, trichloroacetamide, and trichloroacetonitrile to aldehydes.Subsequent 1,2-elimination of the halogen atom and hydroxyl group from the coupling products was also performed with the Pb/Al bimetal system.The technology was successfully applied to stereocontrolled syntheses of ethyl trans- and cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates.

Cyclopropanation process

A process for producing a cyclopropane derivative comprising contacting a diazo compound and an olefinically unsaturated compound in the presence of a catalytic amount of copper cation-exchanged perfluorinated ion exchange polymer is disclosed.

Cyclopropanation of olefins by ethyl diazoacetate: copper- and copper-complex-containing X-zeolites as the catalysts

Cyclopropanation of olefins by ethyl diazoacetate has been carried out making use of the catalytic action of Cu-loaded X-type zeolites upon the decomposition of ethyl diazoacetate.The activity of the NaCuX zeolites is linearly dependent upon the Na-exchange level.Compared to conventional copper catalysts, the zeolite catalysts give rise to relatively low amounts of polymeric side-product which is assumed to be formed at the outer zeolite surface.The stereoselectivity obtained with the zeolite catalysts does not deviate significantly from that obtained using copper salts.Zeolite X, loaded with chiral copper complexes, gives rise to only minor asymmetric induction upon cyclopropanation of 1,1-dichloro-4-methyl-1,3-pentadiene with ethyl diazoacetate.

A Convenient Synthesis of Ethyl 3-(2,2-Dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates and Its Modifications for cis-Isomer Enrichment

A synthesis of the title compounds 5 involves the reaction between 3-methyl-2-buten-1-ol and triethyl orthoacetate to produce ethyl 3,3-dimethyl-4-pentenoate, which is followed by the addition of various carbon tetrahalides to the double bond.The reaction of resulting adducts with a base affords 5 in high yields.Stereoselective preparation of the cis-isomer was achieved by the following two methods: First one involves selective transformation of ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate to ethyl 6,6,6-trichloro-2,3-dimethyl-4-hexanoate (8a) with piperidine followed by the selective conversion of 8a to cis-2,2-dichloroethenyl compound (cis-5a).Second one is based on the stereoselective cyclization of ethyl 4,6,6,6-tetrachloro-3,3-dimethyl-hexanoate (t-BuONa/solvent/HMPA) to ethyl cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate which is transformed into cis-5a without cis-trans isomerisation.

Synthesis of ethyl (+/-)-cis-3-(2,2-dihalogenovinyl)-2,2-dimethylcyclopropanecarboxylate

The two (+/-) cis pyrethroid ethyl esters 2a,b have been synthesized.These esters are obtained via stereoselective ScN' cyclization of 3b to 5b.Desulfonylation of 5b with retention of configuration at low temperature (Na/Hg, -30 deg C) affords (+/-)-cis-chrysanthemonitrile 6.This nitrile is converted into cis aldehyde 7 which by Wittig reaction provides pyrethroid nitriles 8a and 8b, respectively.Finally hydrolysis of the nitrile group gives the esters 2a and 2b in 30percent overall yield from 3b.

Process for the preparation of 1,1-dichloro-alkenes

A process for the preparation of a 1,1-dichloro-alkene of the formula STR1 in which R1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, and R2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, or R1 and R2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, comprising reacting a carbonyl compound of the formula STR2 with a trichloromethanephosphonic acid ester of the formula STR3 in which R3 each individually is an alkyl or phenyl radical, or together are alkanediyl, in the presence of at least an equimolar amount of magnesium. Advantageously, R1 is hydrogen, R2 is a C2 to C5 alkenyl radical or a radical of the formula STR4 Z is a cyano, acetal, carboxyl or C1 to C4 alkoxycarbonyl radical, or a radical of the formula COOM, and M is sodium or potassium, R3 each individually is a C1 to C4 alkyl or phenyl radical, or the two radicals R3 together are C2 to C5 alkanediyl, about 0.95 to 1.4 moles of the trichloromethanephosphonic acid ester and about 1.5 to 4 moles of magnesium are employed per mole of the carbonyl compound, and the reaction is carried out at a temperature between about 0° and 150° C. in a polar aprotic solvent. The products are known intermediates, especially for insecticides.

Preparation of 1,1-dihalogeno-alkenes

In the preparation of a 1,1-dihalogenoalkene of the formula STR1 in which R1 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, and R2 is an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, or R1 and R2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, and X1 and X2 each independently is a halogen atom, wherein a carbonyl compound of the formula STR2 is reacted with a trihalogenoacetate of the formula STR3 in which X3 is a halogen atom, and M≈ is an alkali metal ion or one equivalent of an alkaline earth metal ion, in the presence of an approximately equimolar amount of a phosphorus-containing compound, the improvement which comprises employing as said phosphorus-containing compound a phosphorous acid trialkyl ester or a phosphorous acid triamide and effecting the reaction at a temperature between about 0° and 200° C. A preferred end product is STR4 and the preferred phosphorus-containing compound is trimethyl phosphite, triethyl phosphite, tripropyl phosphite or phosphorous acid tris-dimethyl-amide.