2935-23-1

Basic information

• Product Name: cis-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid
• Synonyms: cis-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;Chrysanthemic acid DL-cis-form;cis-(1)-2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylicacid;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (1R,3S)-rel-;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R,3S)-rel-;Einecs 220-908-2;dl-cis-Form;cis-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylic acid
• CAS NO: 2935-23-1
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23
• EINECS: 220-908-2
• Mol File: 2935-23-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 115-116°
• Boiling Point: 246.4°Cat760mmHg
• Flash Point: 119°C
• Appearance: /
• Density: 1.077g/cm³
• CAS DataBase Reference: cis-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(2935-23-1)
• EPA Substance Registry System: cis-(±)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(2935-23-1)

Safety Data

• Hazardous Substances Data: 2935-23-1(Hazardous Substances Data)

Usage

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

• 764-13-6 2,5-Dimethyl-2,4-hexadiene 
• 27335-32-6 (+)-methyl trans-chrysanthemate 
• 76-02-8 trifluoroacetyl chloride 
• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 627-58-7 2,5-dimethyl-1,5-hexadiene 
• 22841-82-3 4,4,7,7-tetramethyl-3-oxa-bicyclo[4.1.0]heptan-2-one 
• 872195-22-7 2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid dicyclohexylmethyl ester 
• 82528-30-1 5-(2-Hydroxy-2-methyl-propyl)-3,3-dimethyl-3H-pyrazole-4-carboxylic acid methyl ester 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 42221-72-7 4-bromo-2,2,5,5-tetramethylcyclohexane-1,3-dione 
• 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 
• 42050-54-4 4-exo-hydroxy-3,3,6,6-tetramethylbicyclo[3.1.0]hexan-2-one 

Downstream Products

• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 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) 
• 50907-07-8 (+/-)-cis-chrysanthemumic acid-(4-nitro-benzyl ester) 
• 4489-12-7 cis-Chrysanthemic acid chloride 
• 454-25-1 (+/-)-cis-Homochrysanthemsaeure 
• 94672-92-1 cis-N-phenyl chrysanthemamide 
• 14087-70-8 4,4,7,7-tetramethyl-3-oxabicyclo<4.1.0>heptan-2-one 
• 454-25-1 (+)-trans-Homochrysanthemsaeure 
• 454-25-1 (-)-trans-Homochrysanthemsaeure 
• 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 

Relevant articles and documents

STEREOSPECIFIC SYNTHESIS OF CIS-2-ALKENYLCYCLOPROPANE CARBOXYLIC ACIDS; A TOTAL SYNTHESIS OF (+/-)-CIS-CHRYSANTHEMIC ACID

A stereospecific route to cis-2,2-dimethyl-3-alkenyl-cyclopropanecarboxylic Acids is illustrated by a total synthesis of (+/-)-cis-Chrysanthemic Acid (11).The key step consists of an alicyclic Claisen rearrangement of O-silyl enolates derived from appropriately substituted (Z)-4-hexen-6-olides .

A NOVEL APPROACH TO CIS-CHRYSANTHEMIC ACIDS

We describe a short route to (1R, 3S)-cis-chrysanthemic acid (1) from the oxabicyclohexanone (3), itself derived from butenolide (4).

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.