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Ethoxymethylenemalononitrile

Base Information Edit
  • Chemical Name:Ethoxymethylenemalononitrile
  • CAS No.:123-06-8
  • Deprecated CAS:1220632-37-0
  • Molecular Formula:C6H6N2O
  • Molecular Weight:122.126
  • Hs Code.:29269090
  • European Community (EC) Number:204-597-0
  • NSC Number:27792
  • UNII:91PS2PWB1Q
  • DSSTox Substance ID:DTXSID3059551
  • Nikkaji Number:J1.508C
  • Mol file:123-06-8.mol
Ethoxymethylenemalononitrile

Synonyms:ethoxymethylene-MN;ethoxymethylenemalononitrile

Suppliers and Price of Ethoxymethylenemalononitrile
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • EthoxymethyleneMalononitrile
  • 100g
  • $ 120.00
  • TRC
  • EthoxymethyleneMalononitrile
  • 250g
  • $ 270.00
  • TRC
  • EthoxymethyleneMalononitrile
  • 50g
  • $ 85.00
  • TCI Chemical
  • (Ethoxymethylene)malononitrile >98.0%(GC)
  • 25g
  • $ 54.00
  • SynQuest Laboratories
  • 2-(Ethoxymethylidene)malononitrile
  • 500 g
  • $ 330.00
  • SynQuest Laboratories
  • 2-(Ethoxymethylidene)malononitrile
  • 100 g
  • $ 104.00
  • Sigma-Aldrich
  • (Ethoxymethylene)malononitrile 98%
  • 25g
  • $ 49.60
  • Sigma-Aldrich
  • (Ethoxymethylene)malononitrile 98%
  • 100g
  • $ 106.00
  • Medical Isotopes, Inc.
  • EthoxymethyleneMalononitrile
  • 10 g
  • $ 860.00
  • Matrix Scientific
  • Ethoxymethylenemalononitrile 95+%
  • 100g
  • $ 38.00
Total 172 raw suppliers
Chemical Property of Ethoxymethylenemalononitrile Edit
Chemical Property:
  • Appearance/Colour:off white to pale yellow 
  • Vapor Pressure:0.00146mmHg at 25°C 
  • Melting Point:64-66 °C(lit.) 
  • Refractive Index:1.461 
  • Boiling Point:296.1 °C at 760 mmHg 
  • Flash Point:135.1 °C 
  • PSA:56.81000 
  • Density:1.07 g/cm3 
  • LogP:0.95396 
  • Storage Temp.:Inert atmosphere,Room Temperature 
  • Solubility.:DMF, DMSO, Ethanol, Methanol 
  • Water Solubility.:insoluble 
  • XLogP3:0.5
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:2
  • Exact Mass:122.048012819
  • Heavy Atom Count:9
  • Complexity:182
Purity/Quality:

99% *data from raw suppliers

EthoxymethyleneMalononitrile *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn,IrritantXi,Toxic
  • Hazard Codes:Xn,T,Xi 
  • Statements: 22-42/43-23/24/25-43-20/21/22-R42/43-R23/24/25-R22 
  • Safety Statements: 22-36/37-45-36/37/39-26-36-24/25-S45-S36/37/39-S26-S22 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Canonical SMILES:CCOC=C(C#N)C#N
  • General Description Ethoxymethylenemalononitrile is a versatile electrophilic alkene that reacts with nucleophiles such as thioureas to form 2-substituted-4-amino-5-cyanopyrimidines or 2-alkylthio-4-amino-5-cyanopyrimidines under alkaline conditions. It can also hydrolyze into derivatives like hydroxymethylenemalononitrile or malononitrile. Additionally, it participates in cyclization reactions, such as forming α-pyrones when reacted with hydroxylated tropones under acid catalysis, and serves as a key intermediate in synthesizing heterocyclic compounds with potential physiological activity. Its reactivity is influenced by reaction conditions, including solvent choice and reagent addition order.
Technology Process of Ethoxymethylenemalononitrile

There total 13 articles about Ethoxymethylenemalononitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.7%

Guidance literature:
Guidance literature:
With acetic anhydride; at 110 - 140 ℃; Reflux;
Refernces Edit

Synthesis of novel tricyclic 2H,7H-furo[3',4':6,7]cyclohepta-[1,2-b]pyran system

10.1007/s10593-009-0199-5

The research investigates the synthesis of novel tricyclic 2H,7H-furo[3',4':6,7]cyclohepta[1,2-b]pyran systems. The study aims to explore the reactions of 8-hydroxy-1,3-dimethyl-4H-cyclohepta[c]furan-4-one (1) with electrophilic alkenes containing good leaving groups, such as ethoxymethylenemalononitrile and ethoxymethylenecyanoacetate, in the presence of KOH. Contrary to expectations, these reactions produced noncyclic cyanovinyl derivatives as potassium salts (3a and 3b) rather than α-pyrones. However, these derivatives could be cyclized to the target α-pyrones (5a and 5b) under acid-catalyzed conditions. The study also synthesized 3-benzamido-2H-pyran-2-ones (9a-c) from 2-aryl-4-ethoxymethylene-4H-1,3-oxazol-5-ones using a similar scheme. The synthesized compounds, which may possess useful physiological activity, were characterized using spectroscopic methods. The research concludes that hydroxytropone 1 exhibits high nucleophilic reactivity with these electrophiles, leading to the formation of novel condensed α-pyrones and 3-benzamido-2H-pyran-2-ones through base-catalyzed and acid-catalyzed steps.

Synthesis and anticonvulsant activity of N-benzylpyrrolo[2,3-d]-, - pyrazolo[3,4-d]-, and -triazolo[4,5-d]pyrimidines: Imidazole ring-modified analogues of 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine

10.1021/jm00019a019

This research study on the synthesis and anticonvulsant activity of N-benzylpyrrolo[2,3-d]-, pyrazolo[3,4-d]-, and triazolo[4,5-d]pyrimidines, which are imidazole ring-modified analogues of 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine (compound 1). The purpose of the study was to evaluate the impact of isosteric replacements of the imidazole ring atoms on the anticonvulsant activity of these compounds. The analogues were found to be less active than compound 1 against maximal electroshock-induced seizures (MES) in rats when administered orally. The research concluded that the differences in anti-MES activity were not due to variations in pKa or lipophilicity but could be related to the distinct electrostatic isopotential maps of the heterocyclic compounds, suggesting that the electrostatic potential on the surface of these compounds might influence their anticonvulsant activity. Key chemicals used in the synthesis process included various benzyl chlorides, amines, and pyrimidines, as well as reagents like potassium carbonate, ethoxymethylenemalononitrile, and formamide.

Reactions of Ethoxymethylenemalononitrile with Thioureas1

10.1021/jo01060a018

The study investigates the reactions of ethoxymethylenemalononitrile with various chemicals, primarily focusing on its behavior with thioureas in alkaline aqueous solutions. Ethoxymethylenemalononitrile can hydrolyze to form different compounds like hydroxymethylenemalononitrile, malononitrile, or tetracyanopropene, depending on the conditions. When reacted with thioureas, it forms 2-substituted-4-amino-5-cyanopyrimidines if added to the thiourea, and 2-alkylthio-4-amino-5-cyanopyrimidines in the presence of mercaptans or alkylthiour eas. The study also explores the formation of pyridines and their derivatives under various conditions, including the use of different solvents and the order of reagent addition. The products' structures are confirmed through synthesis and analysis, highlighting the versatility of ethoxymethylenemalononitrile in forming diverse nitrogen-containing heterocyclic compounds.

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