5407-83-0

Basic information

• Product Name: Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester
• Synonyms: Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester;2-Cyano-2-cyclopentylidene-acetic acid ethyl ester;.delta.1,.alpha.-Cyclopentaneacetic acid, .alpha.-cyano-, ethyl ester;ethyl 2-cyano-2-cyclopentylideneacetate;ethyl 2-cyano-2-cyclopentylidene-acetate;ethyl 2-cyano-2-cyclopentylidene-ethanoate;MFCD00019318
• CAS NO: 5407-83-0
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Mol File: 5407-83-0.mol

Chemical Properties

• Boiling Point: 292.8°Cat760mmHg
• Flash Point: 134.5°C
• Appearance: /
• Density: 1.116g/cm³
• Vapor Pressure: 0.0018mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester(5407-83-0)
• EPA Substance Registry System: Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester(5407-83-0)

Safety Data

• Hazardous Substances Data: 5407-83-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester is used as a solvent for various chemical reactions, facilitating the process and improving the efficiency of the synthesis.
Used in Paint and Coating Industry:
Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester is used as a key ingredient in the formulation of paints, coatings, and adhesives, enhancing their performance and durability.
Used in Adhesive Industry:
Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester is used as a component in adhesive formulations, contributing to their bonding strength and versatility.
However, it is important to note that this chemical has the potential to cause irritation to the skin, eyes, and respiratory tract upon exposure. It may also be harmful if ingested or inhaled in large quantities. Therefore, proper safety measures and precautions should be taken when handling and using Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester in industrial and laboratory settings to minimize the risk of adverse effects.

InChI:InChI=1/C10H13NO2/c1-2-13-10(12)9(7-11)8-5-3-4-6-8/h2-6H2,1H3

Upstream product

• 110-89-4 piperidine 
• 120-92-3 cyclopentanone 
• 105-56-6 ethyl 2-cyanoacetate 
• 686-33-9 ethyl 2-cyanobut-2-enoate 
• 144918-37-6 1-cyano-1-ethoxycarbonyl-1-butene 

Downstream Products

• 61788-30-5 ethyl α-cyanocyclopentaneacetate 
• 24543-20-2 1,2,2-Tricyan-spiro<2.4>heptan-1-carbonsaeure-aethylester 
• 62953-74-6 ethyl 2-cyano-2-(1-cyanocyclopentyl)acetate 
• 4815-29-6 ethyl 2-amino-4H,5H,6H-cyclopentenothiophene-3-carboxylate 
• 77821-82-0 2-Oxo-4-p-tolyl-7-[1-p-tolyl-meth-(Z)-ylidene]-2,5,6,7-tetrahydro-1H-[1]pyrindine-3-carbonitrile 
• 77821-83-1 4-(4-Chloro-phenyl)-7-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-2-oxo-2,5,6,7-tetrahydro-1H-[1]pyrindine-3-carbonitrile 
• 77821-81-9 7-Benzylidene-3-cyano-2-oxo-4-phenyl-2,5,6,7-tetrahydro-1H-1-pyrindine 
• 126921-96-8 3-oxo-1-phenyl-3,5,6,7-tetrahydro-2H-cyclopenta[c]pyridine-4-carbonitrile 
• 77831-45-9 4-(4-Methoxy-phenyl)-7-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-2,5,6,7-tetrahydro-1H-[1]pyrindine-3-carbonitrile 
• 77821-84-2 4-(3,4-Dimethoxy-phenyl)-7-[1-(3,4-dimethoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-2,5,6,7-tetrahydro-1H-[1]pyrindine-3-carbonitrile 
• 224453-17-2 4-ethoxycarbonyl-2,3-dihydro-2-phenylcyclopenta[c]pyridazine-3-imine 
• 1539-03-3 1-cyanocyclopentaneacetonitrile 
• 126921-97-9 7<1H>thioxo-2-phenyl cyclopenta pyridine-6-carbonitrile 
• 126922-11-0 3-(2-Oxo-propylsulfanyl)-1-phenyl-6,7-dihydro-5H-[2]pyrindine-4-carbonitrile 

Relevant articles and documents

Synthesis of spiro[cycloalkane-pyridazinones] with high Fsp3 character

Background: Nowadays, in course of the drug design and discovery much attention is paid to the physicochemical parameters of a drug candidate, in addition to their biological activity. Disadvantageous physicochemical parameters can hinder the success of a drug candidate. Objective: Lovering et al. introduced the Fsp3 character as a measure of carbon bond saturation, which is related to the physicochemical paramethers of the drug. The pharmaceutical research focuses on the synthesis of compounds with high Fsp3 character. Method: To improve the physicochemical properties (clogP, solubility, more advantageous ADME profile, etc.) of drug-candidate molecules one possibility is the replacement of all-carbon aromatic systems with bioisoster heteroaromatic moieties, e.g. with one or two nitrogen atom containing systems, such as pyridines and pyridazines, etc. The other option is to increase the Fsp3 character of the drug candidates. Both of these aspects were considered in the design the new spiro[cycloalkanepyridazinones], the synthesis of which is described in the present study. Results: Starting from 2-oxaspiro[4.5]decane-1,3-dione or 2-oxaspiro[4.4]nonane-1,3-dione, the corresponding ketocarboxylic acids were obtained by Friedel-Crafts reaction with anisole or veratrole. The ketocarboxylic acids were treated by hydrazine, methylhydrazine or phenylhydrazine to form the pyridazinone ring. N-Alkylation reaction of the pyridazinones resulted in the formation of further derivatives with high Fsp3 character. Conclusion: A small compound library was obtained incorporating compounds with high Fsp3 characters, which predicts advantageous physico-chemical parameters (LogP, ClogP and TPSA) for potential applications in medicinal chemistry.

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes utilizing S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate is an efficient approach to obtain a range of monofluorocyclopropane derivatives. So far, fluoromethylsulfonium salts have displayed the broadest scope for direct fluoromethylene transfer. In contrast to more commonly used fluorohalomethanes or freon derivatives, diarylfluoromethylsulfonium salts are bench stable, easy-to use reagents useful for the direct transfer of a fluoromethylene group to alkenes giving access to the challenging products-fluorocyclopropane derivatives. Interplay between the reactivity of the starting materials and stability of the fluorocyclopropanes formed determines the outcome of the process.

Amino Acid Amide based Ionic Liquid as an Efficient Organo-Catalyst for Solvent-free Knoevenagel Condensation at Room Temperature

Abstract: Ionic liquids of amino acid amide were synthesized and used as an efficient catalyst for solvent-free Knoevenagel condensation. Synthesized ionic liquids are an environmentally benign, inexpensive, metal free and plays the dual role of solvent as well as an efficient catalyst for Knoevenagel condensation. A wide range of aliphatic, aromatic and heteroaromatic aldehydes easily undergo condensation with malononitrile and ethyl cyanoacetate. The reaction proceeds at room temperature without using any organic solvent and is very fast with good to excellent yield. Additionally, the catalyst is easily separable and recyclable without loss of activity. Graphic Abstract: [Figure not available: see fulltext.].

Vanadium-Catalyzed Condensation of Ethyl Cyanoacetate with Ketones

Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75–100% yield.

Polyoxoniobates as a superior Lewis base efficiently catalyzed Knoevenagel condensation

The outstanding basicity of negative charged Lindqvist type Polyoxoniobate K7HNb6O19·13H2O (Nb6) have been proved experimentally as well as by theoretical NBO calculations, the results insights high electron density on terminal and bridging oxygen atoms of niobate anion. The most negative Natural Bond Orbital charge (NBO) of oxygen in Nb6 is ?1.001, which is a much more negative value than those reported in other polyoxometalates, that corroborates its high basicity thus likely to be employed as a strong base catalyst. Experimental study suggests that Nb6 can efficiently catalyze Knoevenagel condensation of various carbonyl compounds with active methylene compounds neglecting the steric and electronic effect of aromatic aldehydes under mild conditions. Kinetic test shows that Knoevenagel condensation of benzaldehyde with ethyl cyanoacetate exhibits second-order kinetics in the presence of Nb6 and the calculated activation energy is 43.3 kJ mol?1. Meanwhile, a proper mechanism according to the NBO study speculates that the most negative charged terminal oxygens in Nb6 would be pivotal in this transformation.

IMINE DERIVATIVES AS HERBICIDAL COMPOUNDS

The invention relates to haloalkysulphonamide derivatives of formula (I) wherein A, W, m, n, p, R, R1, R2, R5, R6, R7, R8 and R9 are as defined in the specification. Furthermore, the present invention relates to processes for making compounds of formula (I), to herbicidal compositions comprising these compounds and to methods of using these compounds to control or inhibit plant growth.

HERBICIDAL COMPOUNDS

The invention relates to haloalkylsulphonamide derivatives of the formula (I) wherein A, W, X, m, n, p, R, R1, R2, R5, R6, R7 and R8 are as defined in the specification. Furthermore, the present invention relates to processes for making compounds of formula (I), to herbicidal compositions comprising these compounds and to methods of using these compounds to control or inhibit plant growth.

HERBICIDAL HALOALKYLSULPHONAMIDE COMPOUNDS

The invention relates to haloalkylsulphonamide derivatives of the formula (I) wherein A, W, X, m, n, p, R, R1, R2, R5, R6, R7and R8 are as defined in the specification. Furthermore, the present invention relates to processes for making compounds of formula (I), to herbicidal compositions comprising these compounds and to methods of using these compounds to control or inhibit plant growth.

Base-free Knoevenagel condensation catalyzed by copper metal surfaces

For the first time Knoevenagel condensation has been catalyzed by elemental copper with unexpected activity and excellent isolated yields. Inexpensive, widely available copper powder was used to catalyze the condensation of cyanoacetate and benzaldehyde under mild conditions. To ensure general applicability, a wide variety of different substrates was successfully reacted.

Aqueous DABCO, an efficient medium for rapid organocatalyzed Knoevenagel condensation and the Gewald reaction

In the presence of water and 1,4-diazabicyclo[2.2.2]octane, several aldehydes and cyclic ketones underwent efficient Knoevenagel condensation with malononitrile and ethyl cyanoacetate to produce the respective α.β-unsaturated systems within fairly short time periods. As a result, high yields of conjugated products were easily obtained. Products could be engaged in a Gewald reaction, either stepwise or in situ, to produce efficiently their respective 2-aminothiophenes within 4-7 h. TUeBITAK.