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
• Article Data: 25

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

General Description

Acetic acid, 2-cyano-2-cyclopentylidene-, ethyl ester, is a chemical compound used primarily as a solvent and intermediate in organic synthesis. It is known for its strong odor and is commonly used in the production of paints, coatings, and adhesives. This chemical has the potential to cause irritation to the skin, eyes, and respiratory tract upon exposure, and may also be harmful if ingested or inhaled in large quantities. As such, caution should be exercised when handling and using this compound in industrial and laboratory settings.

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 
• 144918-37-6 1-cyano-1-ethoxycarbonyl-1-butene 
• 686-33-9 ethyl 2-cyanobut-2-enoate 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 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 
• 61788-30-5 ethyl α-cyanocyclopentaneacetate 
• 68592-07-4 α-cyano-[1-(2-methoxybenzyl)cyclopentane]-acetic acid ethyl ester 
• 1119523-43-1 ethyl 5-amino-6-nitro-7-phenyl-2,3-dihydro-1H-indene-4-carboxylate 
• 24543-20-2 1,2,2-Tricyan-spiro<2.4>heptan-1-carbonsaeure-aethylester 
• 62953-74-6 ethyl 2-cyano-2-(1-cyanocyclopentyl)acetate 
• 5407-84-1 β-phenyl-β,β-tetramethylenepropionitrile 

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.

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.].

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.