Ethyl cyanoacetate

Base Information

• Chemical Name: Ethyl cyanoacetate
• CAS No.: 105-56-6
• Deprecated CAS: 1427280-50-9
• Molecular Formula: C5H7NO2
• Molecular Weight: 113.116
• Hs Code.: H2COOC2H5 MOL WT. 113.12
• European Community (EC) Number: 203-309-0
• NSC Number: 8844
• UN Number: 3276,2666
• UNII: X9N006U0F8
• DSSTox Substance ID: DTXSID9026718
• Nikkaji Number: J4.031B
• Wikipedia: Ethyl_cyanoacetate
• Wikidata: Q1146961
• ChEMBL ID: CHEMBL3186698
• Mol file: 105-56-6.mol

Synonyms:ethyl cyanoacetate;ethyl cyanoacetate, 14C-labeled

Chemical Property of Ethyl cyanoacetate

Chemical Property:

• Appearance/Colour: Clear to very yellow liquid
• Vapor Pressure: 0.275mmHg at 25°C
• Melting Point: -22 °C
• Refractive Index: 1.4175
• Boiling Point: 203.6 °C at 760 mmHg
• PKA: 3.19±0.10(Predicted)
• Flash Point: 84.1 °C
• PSA: 50.09000
• Density: 1.047 g/cm³
• LogP: 0.46318
• Storage Temp.: Store below +30°C.
• Solubility.: 20g/l
• Water Solubility.: 20 g/L (20℃)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 113.047678466
• Heavy Atom Count: 8
• Complexity: 122
• Transport DOT Label: Poison

Purity/Quality:

95%, 99% ^*data from raw suppliers

Ethyl Cyanoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CCOC(=O)CC#N
• Description: Ethyl cyanoacetate is the ethyl ester of cyanoacetic acid. Ethyl cyanoacetate hydrolizes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol (and so it does under most physiological and environmental conditions), while in acid pH the half life is considerably longer. Knoevenagel condensation of ethyl cyanoacetate with aldehyde is reported. Microwave enhanced Knoevenegal condensation reaction of ethyl cyanoacetate with an aldehyde, P2O5, piperidine and chlorobenzene is reported.
• Uses: Ethyl cyanoacetate may be used in the synthesis of ethyl glyoxylate. It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites. Reagent used in labelled pyrimidine and purine synthesis. Ethyl cyanoacetate is an ester. It may be used in the synthesis of ethyl glyoxylate.It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.

Technology Process of Ethyl cyanoacetate

There total 86 articles about Ethyl cyanoacetate 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: 97.0%

ethanol (64-17-5) + cyanoacetic acid amide (107-91-5) → ethyl 2-cyanoacetate (105-56-6)

Guidance literature:

With sulfuric acid; for 3h; Time; Reflux;

Reference yield: 95.0%

ethanol (64-17-5) + cyanoacetic acid (372-09-8) → ethyl 2-cyanoacetate (105-56-6)

Guidance literature:

With sulfuric acid; In dichloromethane; for 18h; Heating;

DOI:10.1002/1099-0690(200207)2002:14<2356::AID-EJOC2356>3.0.CO;2-S

Reference yield: 94.2%

hydrogen cyanide (74-90-8) + chloroacetic acid ethyl ester (105-39-5) → ethyl 2-cyanoacetate (105-56-6)

Guidance literature:

With triethylamine; at 15 ℃; for 4.83333h; Concentration; Reagent/catalyst; Solvent; Temperature; Time;

upstream raw materials:

ethanol

cyanoacetic acid

sodium cyanide

chloroacetic acid ethyl ester

Downstream raw materials:

2-oxotetrahydrofuran-3-carbonitrile

α-cyano-γ,γ-dimethyl-γ-butyrolactone

ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate

(2-ethoxycarbonyl-2-methyl-cyclohexylidene)-cyano-acetic acid ethyl ester

Refernces

• 1、 Kakehi,Ito,Ueda,Takano. "Preparation of new nitrogen-bridged heterocycles. XXXIII. A new preparative method for thieno[3,2-α]indolizines". . p. 1753 - 1756. Retrieved 1993.
• 2、 Levine,Hauser. "-". . p. 760. Retrieved 1946.
• 3、 Chang, Chenyang,Wu, Xinxin,Zhang, Huihui,Zhu, Chen. "Radical trifunctionalization of hexenenitrile via remote cyano migration". supporting information. p. 1005 - 1008. Retrieved 2022/02/01.
• 4、 -. "PROCESS FOR PREPARING CYANOACETATES". Paragraph 0027-0030. . Retrieved 2020/10/27.