Ethyl phenylcyanoacetate

Base Information

• Chemical Name: Ethyl phenylcyanoacetate
• CAS No.: 4553-07-5
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 29269095
• European Community (EC) Number: 224-921-4
• NSC Number: 362
• DSSTox Substance ID: DTXSID101032223
• Nikkaji Number: J122.038A
• Wikidata: Q27122995
• Metabolomics Workbench ID: 57972
• Mol file: 4553-07-5.mol

Synonyms:Ethyl phenylcyanoacetate;Ethyl 2-cyano-2-phenylacetate;4553-07-5;Phenylcyanoacetic acid ethyl ester;Ethyl cyanophenylacetate;ethyl cyano(phenyl)acetate;ethylphenylcyanoacetate;Acetic acid, cyanophenyl-, ethyl ester;Ethyl alpha-cyanophenylacetate;Ethyl alpha-cyano-alpha-phenylacetate;MFCD00001866;alpha-cyanobenzeneacetic acid, ethyl ester;Benzeneacetic acid, .alpha.-cyano-, ethyl ester;ethyl-2-phenylcyanoacetate;Benzeneacetic acid, alpha-cyano-, ethyl ester;SCHEMBL502194;Ethyl alpha-cyanobenzeneacetate;ethyl-2-cyano-2-phenylacetate;Ethyl phenylcyanoacetate, 95%;NSC362;Ethyl .alpha.-cyanophenylacetate;CHEBI:51926;NSC 362;NSC-362;DTXSID101032223;EINECS 224-921-4;AKOS005203415;DS-14028;Ethyl .alpha.-cyano-.alpha.-phenylacetate;AI3-05831;P1255;EN300-66020;Ethyl ester of .alpha.-cyanobenzeneacetic acid;W10859;W-200053;Q27122995

Chemical Property of Ethyl phenylcyanoacetate

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.00523mmHg at 25°C
• Melting Point: 115-116 °C
• Refractive Index: 1.5033-1.5053
• Boiling Point: 275 °C at 760 mmHg
• Flash Point: 137.5 °C
• PSA: 50.09000
• Density: 1.117g/cm³
• LogP: 1.85688
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, DMSO, Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 235

Purity/Quality:

97% ^*data from raw suppliers

Ethyl2-cyano-2-phenylacetate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21-36/37/38-20/21/22
• Safety Statements: 23-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C#N)C1=CC=CC=C1
• General Description: ETHYL PHENYLCYANOACETATE is a substituted cyanoacetate ester that serves as a key substrate in enantioselective catalytic reactions for generating quaternary carbon stereocenters. In the described study, it participates in additions to acetylenic esters, facilitated by a chiral cobalt(III) hydrogen-bond-donor catalyst, yielding high enantioselectivity and Z/E selectivity. The compound's reactivity highlights its utility in asymmetric synthesis, particularly for constructing complex molecular architectures with stereochemical precision.

Technology Process of Ethyl phenylcyanoacetate

There total 27 articles about Ethyl phenylcyanoacetate 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: 93.0%

chlorobenzene (108-90-7) + ethyl 2-cyanoacetate (105-56-6) → ethyl phenylcyanoacetate (4553-07-5)

Guidance literature:

With potassium tert-butylate; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; at 90 ℃; for 5h;

DOI:10.1002/anie.200351954

Reference yield: 91.0%

phenylacetonitrile (140-29-4) → ethyl phenylcyanoacetate (4553-07-5)

Guidance literature:

With polymeric trityllithium; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00415a034

Reference yield: 84.7%

phenylacetonitrile (140-29-4) + Diethyl carbonate (105-58-8,76619-83-5) → ethyl phenylcyanoacetate (4553-07-5)

Guidance literature:

With sodium ethanolate; In toluene; for 2h; Heating;

upstream raw materials:

phenylacetonitrile

Diethyl carbonate

diethyl ether

Natrium-phenylacetonitril

Downstream raw materials:

2,2'-dicyano-2,2'-diphenyl-3,3'-piperazine-1,4-diyl-di-propionic acid diethyl ester

2-cyano-3-(2,6-dioxo-cyclohexyl)-2-phenyl-propionic acid methyl ester

2-cyano-2-phenyldiethyl glutarate

Phenyl-propyl-cyanessigsaeureethylester

Refernces

An Air- and Water-Stable Hydrogen-Bond-Donor Catalyst for the Enantioselective Generation of Quaternary Carbon Stereocenters by Additions of Substituted Cyanoacetate Esters to Acetylenic Esters

10.1002/chem.202001639

The study presents an innovative approach to the enantioselective generation of quaternary carbon stereocenters through the addition of substituted cyanoacetate esters to acetylenic esters, utilizing a chiral enantiopure cobalt(III) complex as a hydrogen bond donor catalyst. The research successfully identifies the cobalt complex Δ-[Co((S,S)-dpen)3]3+ 2Cl–B(C6F5)4– (where dpen = 1,2-diphenylethylenediamine) as an effective catalyst for this reaction, achieving high enantioselectivities (up to 98% ee) and Z/E selectivities (up to 99:1) under optimal conditions. The study also explores the scope of the reaction with various substrates, revealing the catalyst's versatility and its potential for synthetic applications. Additionally, the research delves into the mechanism of the reaction, suggesting that hydrogen bonding between the catalyst's NH groups and the substrates plays a crucial role in the catalytic process. This work significantly advances the field of enantioselective catalysis, providing a new tool for the synthesis of complex molecular structures with quaternary carbon stereocenters.