271241-14-6

Basic information

• Product Name: Dimefluthrin
• Synonyms: Dimefluthrin;[2,3,5,6-Tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate;2,2-diMethyl-3-(2-Methylprop-1-en-1-yl)-1-{[2,3,5,6-tetrafluoro-4-(MethoxyMethyl)phenyl]Methyl}cyclopropane-1-carboxylate;2,3,5,6-Tetrafluoro-4-(MethoxyMethyl)benzyl 2,2-diMethyl-3-(2-Methylprop-1-en-1-yl)cyclopropanecarboxylate;Cyclopropanecarboxylicacid, 2,2-diMethyl-3-(2-Methyl-1-propen-1-yl)-,[2,3,5,6-tetrafluoro-4-(MethoxyMethyl)phenyl]Methyl ester;Dimeflrthrin
• CAS NO: 271241-14-6
• Molecular Formula: C₁₉H₂₂F₄O₃
• Molecular Weight: 374.3697928
• EINECS: 200-001-8
• Mol File: 271241-14-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 352.4 °C at 760 mmHg
• Flash Point: 161.4 °C
• Appearance: /
• Density: 1.255 g/cm³
• Vapor Pressure: 3.84E-05mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: 2-8°C
• Solubility: Benzene, DMSO, Methanol
• BRN: 11644422
• CAS DataBase Reference: Dimefluthrin(CAS DataBase Reference)
• NIST Chemistry Reference: Dimefluthrin(271241-14-6)
• EPA Substance Registry System: Dimefluthrin(271241-14-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 271241-14-6(Hazardous Substances Data)

Usage

Description

Dimefluthrin is a pyrethroid pesticide with a broad spectrum, acting by contact, inhalation and repellent by its strong knockdown and killed capability.

Uses

Dimefluthrin is effective against a broad of pest, including mosquitoes, flies, cockroaches and whitefly, etc. Dimefluthrin also use against cloth damaging Lepidoptera (moths) and cloth damaging Coleoptera (beetles) in indoor situations.Dimefluthrin can be used for the control of insects in indoor, non-food use (residences homes, non-food areas of restaurants, schools, warehouses, hotels).

InChI:InChI=1/C19H22F4O3/c1-9(2)6-12-13(19(12,3)4)18(24)26-8-11-16(22)14(20)10(7-25-5)15(21)17(11)23/h6,12-13H,7-8H2,1-5H3

Synthetic route

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol (83282-91-1) + chrysanthemumic acid (10453-89-1) → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (271241-14-6) + n-propyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

Conditions	Yield
Stage #1: 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol With zircornium(IV) n-propoxide In propan-1-ol; xylene at 143 - 145℃; Stage #2: chrysanthemumic acid With 2,6-di-tert-butyl-4-methyl-phenol In propan-1-ol; xylene at 145 - 147℃; for 8h; Product distribution / selectivity;	A 97% B n/a

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol (83282-91-1) + chrysanthemumic acid (10453-89-1) → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (271241-14-6)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene	70%

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol (83282-91-1) + zirconium(IV) chloride (10026-11-6) + chrysanthemumic acid (10453-89-1) → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (271241-14-6)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene	68%

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol (83282-91-1) + (1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (4489-14-9) + (1R)-cis-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride (53955-46-7) + (1S)-trans-chrysanthemumic acid-chloride (26770-95-6) + (1S)-cis-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride (56650-12-5) → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (271241-14-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 8h;

tetra{2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyloxy}zirconium + chrysanthemumic acid (10453-89-1) → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (271241-14-6)

Conditions	Yield
In propan-1-ol; xylene at 145 - 147℃; for 8h; Product distribution / selectivity;

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol (83282-91-1) + 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride (4489-12-7, 4489-14-9, 26770-95-6, 28684-92-6, 34909-52-9, 51348-74-4, 53955-46-7, 56650-12-5, 14297-81-5) → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (271241-14-6)

Conditions	Yield
With pyridine In tetrahydrofuran

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (271241-14-6) → 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-formylcyclopropanecarboxylate (609346-30-7)

Conditions	Yield
With osmium(VIII) oxide; potassium metaperiodate In tetrahydrofuran; 1,4-dioxane; water at 20℃; for 2h; Heating / reflux;

Upstream product

• 83282-91-1 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol 
• 4489-14-9 (1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride 
• 53955-46-7 (1R)-cis-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride 
• 26770-95-6 (1S)-trans-chrysanthemumic acid-chloride 
• 56650-12-5 (1S)-cis-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride 
• 10453-89-1 chrysanthemumic acid 
• 4489-12-7 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride 
• 10026-11-6 zirconium(IV) chloride 

Downstream Products

• 609346-30-7 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-formylcyclopropanecarboxylate 

Relevant articles and documents

Process for the preparation of carboxylic acid esters

There is provided a process for preparing a carboxylic acid ester of formula (3): R2COOR1 (3) wherein R1 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, and R2 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted, a heteroaryl which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, which process is characterized by the steps of reacting a monohydroxy compound of formula (1): [in-line-formulae]R1OH ??(1) [/in-line-formulae] wherein R1 is as defined above, with a zirconium compound of formula (6): [in-line-formulae]Zr(OR8)4 ??(6) [/in-line-formulae] wherein R8 is an alkyl group or an aryl group which may be substituted and is not the same as R1, to prepare a zirconium catalyst, and reacting a carboxylic acid of formula (2): [in-line-formulae]R2COOH ??(2) [/in-line-formulae] wherein R2 is as defined above, with the monohydroxy compound of formula (1) in the presence of the zirconium catalyst.

Process for producing cyclopropanecarboxylates

There is disclosed a process process for producing a cyclopropanecarboxylate of formula (1): 1which process comprises reacting cyclopropanecarboxylic acid of formula (2): 2with a monohydroxy compound of formula (3): R6OH??(3),in the presence of a catalyst compound comprising an element of to Group 4 of the Periodic Table of Elements.