15641-58-4

Basic information

• Product Name: 2,2,3,3-TETRAMETHYLCYCLOPROPANECARBOXYLIC ACID
• Synonyms: Chrysanthemum Acid;2,2,3,3-Tetramethylcyclopropylcarboxylic acid;2，2，3，3-tetramethylcyclopropan carboxylic acid;2,2,3,3-Tetramethyl-1-cyclopropanecarboxylic acid;Chrysanthemic acid;2,2,3,3-Tetramethylcyclopropane-1-carboxylic acid;3-Carboxy-1,1,2,2-tetramethylcyclopropane;2,2,3,3-Tetramethylcyclopropanecarboxylic acid 99%
• CAS NO: 15641-58-4
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• EINECS: 218-271-0
• Product Categories: Cyclopropanes;Simple 3-Membered Ring Compounds;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 15641-58-4.mol

Chemical Properties

• Melting Point: 120-121 °C(lit.)
• Boiling Point: 204.799 °C at 760 mmHg
• Flash Point: 97.502 °C
• Appearance: /
• Density: 0.999 g/cm³
• Vapor Pressure: 0.106mmHg at 25°C
• Refractive Index: 1.454
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 5.20±0.44(Predicted)
• Water Solubility: Slightly soluble in water. Soluble in methanol, ethanol and acetonitrile.
• CAS DataBase Reference: 2,2,3,3-TETRAMETHYLCYCLOPROPANECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,3,3-TETRAMETHYLCYCLOPROPANECARBOXYLIC ACID(15641-58-4)
• EPA Substance Registry System: 2,2,3,3-TETRAMETHYLCYCLOPROPANECARBOXYLIC ACID(15641-58-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: GZ2083500
• HazardClass: IRRITANT
• Hazardous Substances Data: 15641-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,2,3,3-Tetramethylcyclopropanecarboxylic acid is used as a starting material for the synthesis of central nervous system-active compounds. It serves as a cyclic analogue of the antiepileptic drug, Valproic Acid (V094750), which is beneficial for the development of new medications targeting neurological disorders.
Used in Chemical Synthesis:
2,2,3,3-Tetramethylcyclopropanecarboxylic acid is utilized as a key intermediate in the synthesis of various compounds with potential applications in different fields, such as pharmaceuticals, agrochemicals, and materials science. Its unique structure allows for the creation of novel molecules with diverse properties and functions.

InChI:InChI=1/C8H14O2/c1-7(2)5(6(9)10)8(7,3)4/h5H,1-4H3,(H,9,10)

Upstream product

• 917-64-6 methyl magnesium iodide 
• 3664-56-0 1,3,3-trimethylcyclopropene 
• 124-38-9 carbon dioxide 
• 771-10-8 2,2,3,3-tetramethyl-cyclopropanecarboxylic acid ethyl ester 
• 623-73-4 diazoacetic acid ethyl ester 
• 563-79-1 2,3-Dimethyl-2-butene 
• 504-64-3 carbon suboxide 
• 2415-95-4 ethyl 2,2,3,3-tetramethylcyclopropanecarboxylate 
• 39515-41-8 fenpropathrin 

Downstream Products

• 39515-41-8 fenpropathrin 
• 2415-95-4 ethyl 2,2,3,3-tetramethylcyclopropanecarboxylate 
• 24303-61-5 2,2,3,3-tetramethylcyclopropanecarbonyl chloride 
• 727725-92-0 C₂₀H₂₈N₂O₃ 
• 1093983-51-7 (4-(2-(2-chlorophenyl)quinazolin-4-yl)piperazin-1-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 
• 55265-53-7 2,2,3,3-tetramethyl cyclopropyl carboxamide 
• 902072-89-3 N-(3-trifluoromethylphenyl)-2,2,3,3-tetramethylcyclopropanecarboxamide 
• 902072-59-7 N-(4-nitrophenyl)-2,2,3,3-tetramethylcyclopropanecarboxamide 
• 895727-93-2 N-(3-methylphenyl)-2,2,3,3-tetramethylcyclopropanecarboxamide 
• 309939-30-8 N-(3-nitrophenyl)-2,2,3,3-tetramethylcyclopropanecarboxamide 
• 171722-69-3 N-methyl-2,2,3,3-tetramethylcyclopropane carboxamide 
• 1208117-10-5 C₂₀H₃₀N₂O₄S 
• 1430424-32-0 C₂₁H₂₇N₃O₂ 
• 827319-43-7 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(2,2,3,3-tetramethylcyclopropylcarbonyl)oxy-androsta-1,4-diene-17β-carboxylic acid cyanomethyl ester 

Relevant articles and documents

Characterization of a novel thermophilic pyrethroid-hydrolyzing carboxylesterase from Sulfolobus tokodaii into a new family

A novel gene ST2026 encoding a putative carboxylesterase from the thermophilic crenarchaeota Sulfolobus tokodaii (named EstSt7) was cloned and functionally overexpressed in Escherichia coli. The recombinant enzyme was purified to homogeneity after heat treatment, Ni-NTA affinity and Superdex-200 gel filtration chromatography. EstSt7 showed maximum activity at 80 C over 30 min and had a half-life of 180 min at 90 C. Its enzymatic activity was stable in the pH range of 8.0-10.0 with an optimum at 9.0. The enzyme exhibited significant esterase activity toward various p-nitrophenyl esters and the most preferable substrate was p-nitrophenyl butyrate (kcat/Km of 246.3 s-1 mM-1). In addition, EstSt7 showed high activity and stability against organic solvents (20% and 50% v/v) and detergents (1% and 5% v/v). Furthermore, EstSt7 could efficiently hydrolyze a wide range of synthetic pyrethroids including fenpropathrin, permethrin, cypermethrin, cyhalothrin, deltamethrin and bifenthrin, which makes it a potential candidate for the detoxification of pyrethroids for the purpose of biodegradation. Sequence alignment, phylogenetic analysis and comparison of the conserved motif reveal that this novel carboxylesterase EstSt7 should be grouped into a new bacterial lipase and esterase family.

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.

Experimental and Theoretical Investigations of Ring-Expansion in 1-Methylcyclopropylcarbene

1-Methylcyclopropylcarbene, generated by photolysis of two isomeric hydrocarbon precursors, undergoes ring-expansion, readily to give 1-methylcyclobutene. Experimentally, intramolecular carbon-hydrogen insertions are not observed. Trapping studies with TME demonstrates the formation of the expected cyclopropane adduct, and via a double-reciprocal analysis, the lifetime of 1-methylcyclopropylcarbene was determined to be 12 ns in 1,1,2-trichlorotrifluoroethane. Computational studies show that the barrier to ring-expansion is significantly smaller in 1-methylcyclopropylcarbene than in cyclopropylcarbene. The origin of the increased rate of ring-expansion is due to stabilization of the positive charge that occurs at the incipient tertiary carbon that is attached to the migrating carbon center. Department of Chemistry and Biochemistry,.

Fluorobenzyl esters

A compound of formula: STR1 wherein R is selected from hydrogen, cyano, methyl, and ethynyl, and X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol. The compounds are useful as insecticides and acaricides.

Method for producing cyclopropanecarboxylic acid derivatives

A method for producing 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid and intermediate compounds thereof. The 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid is a very useful intermediate for synthesizing insecticidal and acaricidal compounds of pyrethroid type.

Reaction of Triplet Carbonyl Carbene with Olefins

The gas-phase reaction of C2O(3Σ) with 2,3-dimethyl-2-butene produces 1,1,2,2,6,6,7,7-octamethyldispirooctane-4,8-dione and 2,2,3,3-tetramethylcyclopropanecarboxylic acid as major products rather than the allenic product characteristic of the reaction with simpler substrates.The positive identification of these molecules provides strong evidence for prior formation of the previously postulated cyclopropylideneketene.Further, the rate-determining step for reaction of C2O(3Σ) with the substrate cannot be elimination of CO as has been postulated on the basis of calculations.

Novel process for the preparation of tetra-substituted cyclopropane compounds

A process for the preparation of tetrasubstituted cyclopropane compounds of the formula STR1 wherein Y is selected from the group consisting of --CN and --COOR, R is selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms and R1, R2, R3 and R4 are individually selected from alkyl of 1 to 4 carbon atoms or R1 and R2 or R3 and R4 together with the carbon atoms to which they are attached form a carbon homocycle of 3 to 6 carbon atoms with the 2 substituents not forming the ring being alkyl of 1 to 4 carbon atoms or R1 and R2 on the one hand and R3 and R4 on the other together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms which are useful intermediates for the preparation of insecticidal esters and novel intermediates.

Studies in Decarboxylation. Part 13. The Incursion of a Stepwise Mechanism in the Gas-phase Decarboxylation of Cyclopropylacetic Acids

The cyclopropylacetic acids (I)-(IV) have been decarboxylated in the temperature range 720-820 K.It is demonstrated that at 725 K, 2',2'-dimethylcyclopropylacetic acid is decarboxylated by both concerted and stepwise mechanisms.The latter is favoured by higher temperature.Cyclopropylacetic acid is decarboxylated by the concerted mechanism at 725 K, but also exhibits the stepwise mechanism at higher temperature.

Process for preparing cyclopropane-carboxylic acid esters

A process for preparing an organic acid ester of the formula (I), EQU1 wherein R1 is a hydrogen atom or a methyl group, R2 is a methyl group, a vinyl group, a 2,2-dichlorovinyl group, a 1-propenyl group, a 2-methyl-1-propenyl group, a 2-carbomethoxy-1-propenyl group, a 2-methoxymethyl-1-propenyl group, a 1,3-butadienyl group, a 2-methyl-1,3-butadienyl group or a cyclopentylidenemethyl group when R1 is a hydrogen atom, and R2 is a methyl group when R1 is a methyl group; which comprises reacting an acid of the formula (II), EQU2 wherein R1 and R2 are each as defined above, or its reactive derivative, or mixture of the acid and its reactive derivative with a quaternary ammonium salt of the formula (III), SPC1 wherein X is a halogen atom, A is an alkylamine, pyridine or an N-alkylaniline.