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
• Article Data: 9

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

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 15641-58-4 differently. You can refer to the following data:
1. 2,2,3,3-Tetramethylcyclopropanecarboxylic Acid is the cyclic analogue of the antiepileptic drug, Valproic Acid (V094750). 2,2,3,3-Tetramethylcyclopropanecarboxylic Acid is the starting material used in the synthesis of CNS-active compounds.
2. 2,2,3,3-Tetramethylcyclopropanecarboxylic acid was used as a starting material for the synthesis of central nervous system-active compounds.

Definition

ChEBI: A monocarboxylic acid consisting of cyclopropanecarboxylic acid having four methyl substituents.

General Description

2,2,3,3-Tetramethylcyclopropanecarboxylic acid is an inactive cyclopropyl analog of valproic acid (major antiepileptic drug). Inhibition of histone deacetylases and tumor cells cytotoxicities of 2,2,3,3-tetramethylcyclopropanecarboxylic acid was studied.

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

Upstream product

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

Downstream Products

• 1199943-44-6 (1-pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 
• 1199943-43-5 (1-butyl-1H-indol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone 
• 1199943-42-4 (1-propyl-1H-indole-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 
• 895152-66-6 (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 
• 895155-25-6 (1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 
• 895155-78-9 (2,2,3,3-tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone 
• 895155-95-0 (1-(5-hydroxypentyl)-1H-indol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone 

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.

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,.

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.