20417-61-2

Basic information

• Product Name: ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE
• Synonyms: Cyclopropanecarboxylic acid, 2-formyl-, ethyl ester;ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE;Ethyl 2-formyl-1-cyclopropanecarboxylate,predominantly trans;ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE , 96%, PREDOMINANTLY TRANS;2-Formylcyclopropane-1-carboxylic acid ethyl ester;2-Formylcyclopropanecarboxylic acid ethyl ester;ethyl 2-formylcyclopropanecarboxylate;Einecs 243-805-4
• CAS NO: 20417-61-2
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• EINECS: 243-805-4
• Product Categories: Aldehydes;C7;Carbonyl Compounds;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 20417-61-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 60-65 °C0.6 mm Hg(lit.)
• Flash Point: 184 °F
• Appearance: /
• Density: 1.074 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0375mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE(20417-61-2)
• EPA Substance Registry System: ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE(20417-61-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 20417-61-2(Hazardous Substances Data)

Usage

Description

ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE is a chemical compound formed by an acid-catalyzed reaction between acrolein and ethyl diazoacetate. It serves as a reagent in the design, synthesis, and biological evaluation of first-in-class dual-acting histone deacetylase (HDACs) and phosphodiesterase 5 (PDE5) inhibitors for the treatment of Alzheimer's disease.

Uses

Used in Pharmaceutical Industry:
ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE is used as a reagent for the design and synthesis of dual-acting HDAC and PDE5 inhibitors, which are being evaluated for their potential in treating Alzheimer's disease.
Used in Chemical Synthesis:
ETHYL 2-FORMYL-1-CYCLOPROPANECARBOXYLATE is used in the preparation of ethyl trans-2-(4-(methylphenyl)sulfonyl-4,5-dihydrooxazol-5-yl)cyclopropanecarboxylate, a compound that may have potential applications in various chemical processes or industries.

InChI:InChI=1/C7H10O3/c1-2-10-7(9)6-3-5(6)4-8/h4-6H,2-3H2,1H3

Upstream product

• 15224-11-0 trans-ethyl 2-hydroxymethyl-1-cyclopropanecarboxylate 
• 387845-28-5 ethyl 2-((benzyloxy)methyl)cyclopropane-1-carboxylate 
• 7380-81-6 ethyl (dimethylsulfuranylidene)acetate 
• 107-02-8 acrolein 
• 623-73-4 diazoacetic acid ethyl ester 
• 107-18-6 allyl alcohol 

Downstream Products

• 1354692-88-8 4-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-1-(2-ethoxycarbonyl-cyclopropylmethyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoic acid methyl ester 
• 15224-11-0 ethyl (1S*,2S*)-2-(hydroxymethyl)cyclopropane-1-carboxylate 
• 89887-40-1 ethyl trans-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate 
• 89827-99-6 ethyl cis-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate 
• 76834-78-1 ethyl 3-(5-Methoxy-1H-indol-3-yl)propionate 
• 1087347-33-8 tert-butyl (3R,4S)-3-{[[3-{[(1R,2R)-2-({[(5R)-5,6-bis(nitrooxy)hexyl]oxy}carbonyl)cyclopropyl]methoxy}-5-(3-methoxypropyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate 
• 1087347-32-7 tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate 
• 1087347-31-6 tert-butyl (3R,4S)-3-({cyclopropyl-[3-[((1R,2R)-2-{[2-(dimethylamino)-2-oxo-ethoxy]carbonyl}cyclopropyl)methoxy]-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate 
• 1087347-30-5 (1R,2R)-2-{[3-{[[((3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2.6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidin-3-yl)carbonyl](cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropane-1-carboxylic acid 
• 1087347-05-4 ethyl (1R,2R)-2-{[3-({(cyclopropyl)[((3R,4S)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidin-3-yl)carbonyl]amino}methyl)-5-(3-methoxypropyl)phenoxy]methyl}cyclopropane-1-carboxylate 

Relevant articles and documents

Anhydrous Hydrogen Iodide-Mediated Reductive Indolization of in Situ-Generated Cyclopropyl Hydrazones

Fischer-type indolization of N-aryl-C-cyclopropyl hydrazones generated in situ followed by chemoselective reduction using tert-butyl iodide as an anhydrous HI generator was developed. This protocol provides indoles bearing carboxylic acid derivative units. A series of control experiments indicated the HI-mediated formation and reduction of spirocyclopropyl indolenines. Anhydrous HI functions as a Br?nsted acid as well as a reducing agent, facilitating the successful conversion of unstable reaction intermediates and iodinated mixtures in equilibrium.

Photo/N-Heterocyclic Carbene Co-catalyzed Ring Opening and γ-Alkylation of Cyclopropane Enal

An unprecedented photo/NHC-co-catalyzed ring-opening C-C bond cleavage of cyclopropane enal and the following γ-alkylation with a halogenated compound via radicals were established, affording the corresponding γ-alkylated α,β-unsaturated esters in moderate to good yields.

Acid catalyzed reactions of α,β-unsaturated aldehydes and ethyl diazoacetate

The formation of cyclopropanes from α,β-unsaturated aldehydes and diazo compounds has been a rather challenging goal due to the extremely reactive aldehyde starter. Herein, our group reports the first formation of ethyl 2-formyl-1-cyclopropanecarboxylate in 100% yield from the acid catalyzed reaction between acrolein and ethyl diazoacetate (EDA).