53528-32-8

Basic information

• Product Name: Phenothrin
• Synonyms: (±)-cis,trans-2,2-Dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic Acid m-Phenoxybenzyl Ester; 2,2-Diméthyl-3-(2-méthyl-1-propèn-1-yl)cyclopropanecarboxylate de 3-phénoxybenzyle; 247-404-5; 3-Phenoxybenzyl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate; 3-Phenoxybenzyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate; 3-Phenoxybenzyl cis,trans-Chrysanthemate; 3-Phenoxybenzyl-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropancarboxylat; 3-Phenoxybenzyl-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropancarboxylat; 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• CAS NO: 53528-32-8
• Molecular Formula: C₂₃H₂₆O₃
• Molecular Weight: 350.45
• EINECS: 247-404-5
• Mol File: 53528-32-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Phenothrin(CAS DataBase Reference)
• NIST Chemistry Reference: Phenothrin(53528-32-8)
• EPA Substance Registry System: Phenothrin(53528-32-8)

Safety Data

• Hazardous Substances Data: 53528-32-8(Hazardous Substances Data)

Upstream product

• 594-16-1 2,2-dibromopropane 
• 10231-96-6 1-carbethoxy-5-methylhexa-2,4-diene 
• 4489-12-7 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride 
• 13826-35-2 3-Phenoxybenzyl alcohol 
• 4489-14-9 (1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride 
• 79-37-8 oxalyl dichloride 
• 884846-74-6 vinyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 
• 13499-05-3 hafnium tetrachloride 
• 10453-89-1 chrysanthemumic acid 
• 10026-11-6 zirconium(IV) chloride 

Downstream Products

• 52611-74-2 (1R,3R)-3-((S)-3,3-Dimethyl-oxiranyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 52611-73-1 (1R,3R)-3-((R)-3,3-Dimethyl-oxiranyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 146205-06-3 (1R,3R)-3-((E)-2-Formyl-3-hydroxy-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 145551-95-7 (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxo-propenyl)-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 
• 145551-94-6 (1R,3R)-3-((E)-3-Hydroxy-2-methyl-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester 

Relevant articles and documents

Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes

Dimethylcyclopropanes are valuable synthetic targets that are challenging to access in high yield using Zn carbenoid reagents. Herein, we describe a cobalt-catalyzed variant of the Simmons–Smith reaction that enables the efficient dimethylcyclopropanation of 1,3-dienes using a Me2CCl2/Zn reagent mixture. The reactions proceed with high regioselectivity based on the substitution pattern of the 1,3-diene. The products are vinylcyclopropanes, which serve as substrates for transition-metal-catalyzed ring-opening reactions, including 1,3-rearrangement and [5+2] cycloaddition. Preliminary studies indicate that moderately activated monoalkenes are also amenable to dimethylcyclopropanation under the conditions of cobalt catalysis.

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.

Three-Bond 13C-1H Coupling Constants for Chrysanthemic Acid and Phenothrin Metabolites: Detection by Two-Dimensional Long-Range 13C-1H J-Resolution Spectroscopy

Two-dimensional long-range 13C-1H J-resolution spectroscopy (LRCJR) was used to measure three-bond 13C-1H coupling constants 3J(C,H)> for trans- and cis-chrysanthemic acid, methyl trans-pyrethrate and some microsomal metabolites of the trans-chrysanthemate biophenothrin.The carbon of the methyl cis-disposed to an attached proton shows a larger 3J(C,H) value than does the trans-carbon for the dimethyl-substituted cyclopropane and epoxide rings.The reverse situation applies for the analogous dimethyl vinyl grouping.The 3J(C,H) values are not altered on conversion of one of the olefinic geminal methyl groups to a hydroxymethyl or methoxycarbonyl functionality, but increase on transformation to an aldehyde.These 3J(C,H) values are in agreement with previous results from long-range C-H COSY experiments, and provide a useful method for determining the stereochemistry of chrysanthemic acid derivatives. KEY WORDS: Long-range 13C-1H coupling constants, Long-range 13C-1H J-resolution spectroscopy, Chrysanthemic acid, Pyrethroid, 2D NMR