17447-60-8

Basic information

• Product Name: 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester
• Synonyms: 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester;dimethyl 2-vinylcyclopropane-1,1-dicarboxylate;Dimethyl 2-ethenylcyclopropane-1,1-dicarboxylate, 95%
• CAS NO: 17447-60-8
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.18918
• Mol File: 17447-60-8.mol
• Article Data: 40

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Ethyl Acetate; Dichloromethane
• CAS DataBase Reference: 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester(17447-60-8)
• EPA Substance Registry System: 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester(17447-60-8)

Safety Data

• Hazardous Substances Data: 17447-60-8(Hazardous Substances Data)

Usage

Description

2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester, also known as 1,1-Dimethyl 2-Ethenylcyclopropane-1,1-dicarboxylate, is an organic compound that serves as an important intermediate in the synthesis of various chemical products. It is characterized by its unique cyclopropane ring and vinyl group, which provide it with versatile reactivity and potential applications in different industries.

Uses

Used in Organic Synthesis:
2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of reactions, making it a valuable building block for the creation of complex molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is used as a starting material for the development of new drugs. Its versatile chemical properties enable the synthesis of a variety of drug candidates with potential therapeutic applications.
Used in Chemical Research:
2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic pathways. Its unique structure provides researchers with valuable insights into the behavior of similar compounds and the development of novel synthetic strategies.
Used in Material Science:
In the field of material science, 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester can be used as a monomer for the production of polymers with specific properties. Its incorporation into polymer structures can lead to materials with enhanced mechanical, thermal, or electrical characteristics, depending on the desired application.
Overall, 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is a versatile and valuable compound with a wide range of applications across various industries, including organic synthesis, pharmaceuticals, chemical research, and material science. Its unique structure and reactivity make it an essential component in the development of new products and technologies.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3825, 1985 DOI: 10.1016/S0040-4039(00)89261-8

Upstream product

• 6773-29-1 dimethyl diazomalonate 
• 106-99-0 buta-1,3-diene 
• 764-41-0 1,4-dichloro-2-butene 
• 108-59-8 malonic acid dimethyl ester 
• 102060-82-2 (E)-dimethyl 2-(4-((methoxycarbonyl)oxy)but-2-en-1-yl)malonate 
• 292638-85-8 acrylic acid methyl ester 
• 1476-11-5 Z-1,4-dichlorobutene 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 821-06-7 (E)-1,4-dibromobutene 
• 5332-81-0 carbonic acid (Z)-4-methoxycarbonyloxy-but-2-enyl ester methyl ester 
• 166302-33-6 2-(2-Hydroxy-1-trimethylsilanyl-ethyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester 
• 40637-56-7 dimethyl allylmalonate 
• 51534-74-8 dimethyl 3-oxopropane-1,1-dicarboxylate 
• 166302-22-3 2-(Carboxy-trimethylsilanyl-methyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester 

Downstream Products

• 100520-02-3 1-butoxy-2-phenylsulfanyl-ethane 
• 128065-32-7 dimethyl 3-butoxy-4-vinylcyclopentane-1,1-dicarboxylate 
• 128065-21-4 1,1-dimethoxycarbonyl-3-p-toluenesulfonylmethyl-4-vinylcyclopentane 
• 128065-22-5 1,1-dimethoxycarbonyl-3-methyl-3-p-toluenesulfonyl-4-vinylcyclopentane 
• 99260-82-9 2-((E)-5,5-Bis-benzenesulfonyl-pent-2-enyl)-malonic acid dimethyl ester 
• 99260-87-4 (4E,9E)-7,7-Bis-benzenesulfonyl-2,12-bis-methoxycarbonyl-trideca-4,9-dienedioic acid dimethyl ester 
• 57742-48-0 (RS)-2-Vinyl-1,1-cyclopropandicarbonsaeure 
• 112723-48-5 1-(4-Nitro-phenyl)-2-oxo-5-vinyl-pyrrolidine-3,3-dicarboxylic acid dimethyl ester 
• 112723-44-1 N-phenyl-2,2-bis(methoxycarbonyl)-4-vinylbutyrolactam 
• 112723-47-4 1-(4-Methoxy-phenyl)-2-oxo-5-vinyl-pyrrolidine-3,3-dicarboxylic acid dimethyl ester 
• 112723-49-6 2,2-diphenyl-5,5-bis(methoxycarbonyl)-3-vinylcyclopentanone 
• 158665-21-5 2-ethenylcyclopropane-1,1-dicarboxamide 
• 497179-34-7 dimethyl 2-[2-(3-allyl-1-benzyl-1H-indol-2-yl)-3-butenyl]malonate 

Relevant articles and documents

Indium(III) Chloride-Promoted Intramolecular Addition of Allylstannanes to Alkynes

In the presence of an equimolar amount of InCl3, 8-tributylstannyl-6-octen-1-ynes (allylstannanes bearing an alkynyl group) were efficiently cyclized to 2-allyl-1-methylenecyclopentanes. In contrast, catalytic use of InCl3 gave 2-all

Palladium-catalyzed diastereo- And enantioselective [3 + 2] cycloaddition of vinylcyclopropanes with azadienes: Efficient access to chiral spirocycles

Benzofuran-derived azadienes (BDAs) have been widely used as four-atom synthons in transition-metal-mediated cycloaddition reactions, while the exploitation of their reactivity as a two-atom unit to construct spirocycles is still underdeveloped. Herein, we reported the first palladium(0)-catalyzed diastereo- and enantioselective [3 + 2] annulation of vinylcyclopropanes (VCPs) and BDAs. This transformation is featured with a broad substrate scope (31 examples), allowing for facile access to a variety of enantioenriched spirocycles bearing a quaternary stereogenic center in good yields with excellent regio-, diastereo-, and enantioselectivities (up to 93% yield, >20:1 dr, and mostly >99% ee) under mild reaction conditions. Moreover, the spirocyclic products could be efficiently converted to structurally complex tricyclo[8.3.0.01,5]-azatridecane and tricyclo[7.3.0.01,5]-azadodecane skeletons.

Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis

A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine

A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.