26771-06-2

Basic information

• Product Name: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid
• Synonyms: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid;(1S)-2,2-Dimethyl-3α-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;(1S)-2β-(2-Methyl-1-propenyl)-3,3-dimethylcyclopropane-1β-carboxylic acid;(1S,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid
• CAS NO: 26771-06-2
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 247-994-4
• Mol File: 26771-06-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 246.4°Cat760mmHg
• Flash Point: 119°C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 0.0088mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(26771-06-2)
• EPA Substance Registry System: (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid(26771-06-2)

Safety Data

• Hazardous Substances Data: 26771-06-2(Hazardous Substances Data)

Usage

Description

(1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid is an organic compound characterized by its unique cyclopropane carboxylic acid structure, featuring two methyl groups and an isopropyl group attached to the cyclopropane ring. With a molecular formula of C11H18O2, this colorless liquid at room temperature is a versatile building block in organic synthesis and medicinal chemistry research.

Uses

Used in Pharmaceutical Synthesis:
(1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its distinctive structure and properties contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, (1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid serves as a crucial component in the production of pesticides and other agrochemicals. Its incorporation aids in enhancing the effectiveness and selectivity of these products for agricultural use.
Used in Organic Synthesis Research:
(1S-cis)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid is employed as a valuable building block in organic synthesis research. Its unique structure allows for the exploration of new synthetic pathways and the creation of novel compounds with potential applications across various industries.

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-/m1/s1

Upstream product

• 19902-09-1 (+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide 
• 5460-63-9 chrysanthemumic acid methyl ester 
• 97-41-6 ethyl trans-(+/-)-chrysanthemate 
• 97-41-6 ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate 
• 19165-55-0 2,2,5,5-tetramethylcyclohex-3-en-1-ol 
• 15500-76-2 Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) 
• 702-50-1 2,2,5,5-tetramethylcyclohexa-1,3-dione 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 78779-89-2 (+/-)-trans-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide 
• 2198-88-1 (+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile 
• 764-13-6 2,5-Dimethyl-2,4-hexadiene 
• 627-58-7 2,5-dimethyl-1,5-hexadiene 
• 142-30-3 2,5-dihydroxy-2,5-dimethyl-3-hexyne 
• 75646-37-6 Acetic acid (Z)-4-hydroxy-1,1,4-trimethyl-pent-2-enyl ester 

Downstream Products

• 5460-63-9 methyl (dl)-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) 
• 29172-41-6 trans-chrysanthemyl acetate 
• 42077-38-3 C₁₈H₂₆N₂O₂S 
• 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

Total Syntheses of All Six Chiral Natural Pyrethrins: Accurate Determination of the Physical Properties, Their Insecticidal Activities, and Evaluation of Synthetic Methods

Chiral total syntheses of all six insecticidal natural pyrethrins (three pyrethrin I and three pyrethrin II compounds) contained in the chrysanthemum (pyrethrum) flower were performed. Three common alcohol components [(S)-cinerolone, (S)-jasmololone, and (S)-pyrethrolone] were synthesized: (i) straightforward Sonogashira-type cross-couplings using available (S)-4-hydroxy-3-methyl-2-(2-propynyl)cyclopent-2-en-1-ones (the prallethrin alcohol) for (S)-cinerolone (overall 52% yield, 98% ee) and (S)-pyrethrolone (overall 54% yield, 98% ee) and (ii) traditional decarboxylative-aldol condensation and lipase-catalyzed optical resolution for (S)-jasmololone (overall 16% yield, 96% ee). Two counter acid segments [(1R,3R)-chrysanthemic acid (A) and (1R,3R)-second chrysanthemic acid precursor (B)] were prepared: (i) C(1) epimerization of ethyl (±)-chrysanthemates and optical resolution using (S)-naphthylethylamine to afford A (96% ee) and (ii) concise derivatization of A to B (96% ee). All six pyrethrin esters (cinerin I/II, jasmolin I/II, and pyrethrin I/II) were successfully synthesized utilizing an accessible esterification reagent (TsCl/N-methylimidazole). To investigate the stereostructure-activity relationship, all four chiral stereoisomers of cinerin I were synthesized. Three alternative syntheses of (±)-jasmololone were investigated (methods utilizing Piancatelli rearrangement, furan transformation, and 1-nitropropene transformation). Insecticidal activity assay (KD50 and IC50) against the common mosquito (Culex pipiens pallens) revealed that (i) pyrethrin I > pyrethrin II, (ii) pyrethrin I (II) > cinerin I (II) ? jasmolin I (II), and (iii) "natural" cinerin I ? three "unnatural" cinerin I compounds (apparent chiral discrimination).

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.

Unprecedented dual reactivity of anhydrous potassium hydroxide in cascade cyclopropannelation/Haller-Bauer-scission/Grob-fragmentation reactions

We report an unprecedented type of reactivity of 'anhydrous potassium hydroxide' ('APH') in which it plays, over a large variety of related educts, sequentially the role of base and nucleophile. Some insight into the structure of reactive species as well as comparative reactivity of related reagents prepared by fusion of commercially available potassium hydroxide or by adding stoichiometric amount of water to potassium hydride is provided.