26771-11-9

Basic information

• Product Name: (1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid
• Synonyms: (1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;(1R)-2,2-Dimethyl-3β-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;(1R)-2,2-Dimethyl-3β-isobutenylcyclopropane-1β-carboxylic acid;(1R)-3,3-Dimethyl-2α-(2-methyl-1-propenyl)cyclopropane-1α-carboxylic acid;(1R,3S)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;2,2-Dimethyl-3β-(2-methyl-1-propenyl)-1β-cyclopropanecarboxylic acid;3,3-Dimethyl-2α-(2-methyl-1-propenyl)-1α-cyclopropanecarboxylic acid
• CAS NO: 26771-11-9
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 247-996-5
• Mol File: 26771-11-9.mol
• Article Data: 30

Chemical Properties

• Melting Point: 41°C
• Boiling Point: 257.18°C (rough estimate)
• Flash Point: 119°C
• Appearance: /
• Density: 0.9812 (rough estimate)
• Refractive Index: 1.4571 (estimate)
• CAS DataBase Reference: (1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(26771-11-9)
• EPA Substance Registry System: (1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(26771-11-9)

Safety Data

• Hazardous Substances Data: 26771-11-9(Hazardous Substances Data)

Usage

Description

(1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid, also known as (+)-cis-Chrysanthemic Acid, is an organic compound that serves as a key intermediate in the synthesis of various chemical compounds. It is characterized by its unique cyclopropane ring structure and multiple methyl groups, which contribute to its chemical properties and reactivity.

Uses

Used in Pesticide Synthesis:
(1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid is used as an intermediate in the synthesis of (+)-cis-Phenothrin (P318100), an isomer of Phenothrin (P318095). (1R-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid is a pesticide that is utilized for the control of pests and insects in various agricultural and domestic settings. Its effectiveness in pest control is attributed to its ability to interfere with the nervous systems of insects, leading to paralysis and death.

InChI:InChI=1/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)/t7?,8-/m0/s1

Upstream product

• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 82442-69-1 (-)-(1R,3S)-cis-2,2-dimethyl-3-(hydroxymethyl)cyclopropanoate 
• 55701-02-5 methyl (1R,3S)-3-formyl-2,2-dimethylcyclopropanecarboxylate 
• 54878-04-5 3-acetoxymethyl-2,2-dimethylcyclopropane-cis-1-(2'-methyl)propan-2'-ol 
• 764-13-6 2,5-Dimethyl-2,4-hexadiene 
• 35059-50-8 t-butyl diazoacetate 
• 78715-54-5 tert-amyl trans-chrysanthemate 
• 2198-88-1 (+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile 
• 78779-89-2 (+/-)-trans-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 62393-91-3 (1R,3S)-2,2-dimethyl-3-(2-hydroxy-2-methylpropyl)-1-(2-oxopropyl)cyclopropane 
• 135516-88-0 3-((1S,3R)-3-[1,3]Dioxolan-2-yl-2,2-dimethyl-cyclopropyl)-2-methyl-propionic acid methyl ester 
• 72367-69-2 3-((1S,3R)-3-Formyl-2,2-dimethyl-cyclopropyl)-2-methyl-propionic acid methyl ester 
• 135516-87-9 3-((1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropyl)-2-methyl-propionic acid methyl ester 

Downstream Products

• 5460-63-9 methyl (dl)-trans-chrysanthemate 
• 14087-70-8 (+)-Dihydrochrysanthemolactone 
• 2259-14-5 (1S,3S)-trans-chrysanthemic acid 
• 4638-92-0 (1R,3R)-trans-chrysanthemic acid 
• 454-25-1 (+/-)-trans-Homochrysanthemsaeure 
• 497-96-1 (+/-)-trans-(E)-pyrethricsaeure 
• 94672-92-1 (+/-)-2.2-dimethyl-3t-(2-methyl-propenyl)-cyclopropane-carbanilide-(1r) 
• 53179-78-5 2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid 
• 25402-06-6 (S)-3-((Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl(1R,3R) -2,2-dimethyl-3-(2-methylprop-1-en-1-yl ) -cyclopropane-1-carboxylate 
• 121-21-1 pyrethrin I 
• 121-20-0 cinerin II 
• 1172-63-0 jasmolin II 
• 121-29-9 Pyrethrin II 
• 93132-69-5 (1R,3R)-2,2-Dimethyl-3-((E)-2-methyl-3-oxoprop-1-en-1-yl)cyclopropane-1-carboxylic Acid 

Relevant articles and documents

Novel Enantioselective Syntheses of Optically Active (1R)-cis- and (1R)-trans-Chrysanthemic Acids.

Dimethyl dimedone, a non chiral and cheap compound, has been converted to the optically actives 1-(R)-cis- and 1-(R)-trans-chrysanthemic acids possessing high economic value.These processes involve as the key steps (i) a cyclopropanation reaction (ii) a Grob fragmentation and (iii) a lipase monitored hydrolysis of a prochiral diacetate.

Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination

An operationally simple method to affect an atom-transfer radical addition of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron-deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.

Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol

2,2,5,5-Tetramethylcyclohexane-1,3-dione is a valuable starting-material precursor of cis-chrysanthemic acid. The (1S)-stereoisomer is a precursor of pyrethrin I, the most active natural insecticide from Chrysanthemum cinerariifolium, whereas the (1R)-stereoisomer is efficiently transformed to deltamethrin, the most active commercially available pyrethroid insecticide. Several intermediates have been identified and used with variable success for that purpose.