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

Uses

(+)-cis-Chrysanthemic Acid is an intermediate in synthesizing (+)-cis-Phenothrin (P318100), an isomer of Phenothrin (P318095), which is a pesticide used in the control of pests and insects.

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

• 127851-86-9 2,2-dimethyl-3-(1-hydroxy-2-methyl-2-propen-1-yl)-1-cyclopropanecarboxylic acid lactone 
• 140695-03-0 (1R,4S,5S)-4-exo-(mesyloxy)-3,3,6,6-tetramethylbicyclo[3.1.0]hexan-2-one 
• 10453-89-1 chrysanthemumic acid 
• 148410-05-3 4-exo-hydroxy-3,3,6,6-tetramethylbicyclo[3.1.0]hexan-2-one 
• 5460-63-9 chrysanthemumic acid methyl ester 
• 83999-42-2 3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 702-50-1 2,2,5,5-tetramethylcyclohexa-1,3-dione 
• 15500-76-2 Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) 
• 19165-55-0 2,2,5,5-tetramethylcyclohex-3-en-1-ol 
• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 764-13-6 2,5-Dimethyl-2,4-hexadiene 
• 76-02-8 trifluoroacetyl chloride 
• 872195-22-7 2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid dicyclohexylmethyl ester 

Downstream Products

• 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) 
• 18228-69-8 rac-trans-1-(-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)ethanone 
• 2861-25-8 trans-chrysanthemyl alcohol 
• 29172-41-6 trans-chrysanthemyl acetate 
• 5460-63-9 methyl (dl)-trans-chrysanthemate 
• 14087-70-8 (+)-Dihydrochrysanthemolactone 
• 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 

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.