Ethyl cyano(ethoxymethylene)acetate

Base Information

• Chemical Name: Ethyl cyano(ethoxymethylene)acetate
• CAS No.: 42466-69-3
• Molecular Formula: C8H11NO3
• Molecular Weight: 169.17800
• NSC Number: 62026,31579,27797
• UNII: 39N7KQP23A
• Nikkaji Number: J2.133.164C
• Wikidata: Q27894437
• Mol file: 42466-69-3.mol

Synonyms:42466-69-3;(Z)-ethyl 2-cyano-3-ethoxyacrylate;ethyl (Z)-2-cyano-3-ethoxyprop-2-enoate;39N7KQP23A;(Z)-2-CYANO-3-ETHOXY-2-PROPENOIC ACID ETHYL ESTER;ethyl (2Z)?-?2-?cyano-?3-?ethoxyacrylate;Ethyl cyano(ethoxymethylene)acetate;Ethyl 2-cyano-3-ethoxyacrylate, (2Z)-;Ethyl (Z)-2-cyano-3-ethoxy-2-propenoate;Ethyl ethoxymethylenecyanoacetate;2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester, (Z)-;2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester, (2Z)-;ethyl (2Z)-2-cyano-3-ethoxyprop-2-enoate;Ethyl .alpha.-(ethoxymethylene)-.alpha.-cyanoacetate;ETHYL (2Z)-2-CYANO-3-ETHOXYACRYLATE;UNII-39N7KQP23A;SCHEMBL167036;(Z)-ethyl2-cyano-3-ethoxyacrylate;NSC27797;NSC31579;NSC62026;NSC-27797;NSC-31579;NSC-62026;(2Z)-ethyl 2-cyano-3-ethoxyacrylate;AKOS016347384;AS-76937;(Z)-2-Cyano-3-ethoxyacrylic acid ethyl ester;D75147;EN300-333496;ethyl (2Z)-2-cyano-3-(ethyloxy)-2-propenoate;Q27894437;(Z)-ETHYL 2-CYANO-3-ETHOXYACRYLATE (Z/E=93/7)

Chemical Property of Ethyl cyano(ethoxymethylene)acetate

Chemical Property:

• Boiling Point: 305.1±0.0 °C(Predicted)
• PSA: 59.32000
• Density: 1.075±0.06 g/cm3(Predicted)
• LogP: 0.99348
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 169.07389321
• Heavy Atom Count: 12
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

(Z)-Ethyl2-cyano-3-ethoxyacrylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC=C(C#N)C(=O)OCC
• Isomeric SMILES: CCO/C=C(/C#N)\C(=O)OCC

Technology Process of Ethyl cyano(ethoxymethylene)acetate

There total 7 articles about Ethyl cyano(ethoxymethylene)acetate 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: 88.1%

orthoformic acid triethyl ester (122-51-0) + ethyl 2-cyanoacetate (105-56-6) → ethyl (ethoxymethylene)cyanoacetate (94-05-3,42466-69-3)

Guidance literature:

orthoformic acid triethyl ester; ethyl 2-cyanoacetate; With acetic acid; at 125 ℃; for 1h; Large scale;

With acetic acid; for 20h; Temperature; Reflux; Large scale;

Reference yield: 60.0%

orthoformic acid triethyl ester (122-51-0) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-3-ethoxyacrylic acid ethyl ester (94-05-3,42466-69-3)

Guidance literature:

With acetic anhydride; at 140 ℃; for 5h;

Reference yield: 47.0%

acetic anhydride (108-24-7) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-3-ethoxyacrylic acid ethyl ester (94-05-3,42466-69-3)

Guidance literature:

With Trimethyl orthoacetate; at 140 ℃;

upstream raw materials:

orthoformic acid triethyl ester

ethyl 2-cyanoacetate

acetic anhydride

Downstream raw materials:

ethyl 4-amino-2-thioxo-1H-pyrimidine-5-carboxylate

2-cyano-3-(4-thiazol-2-ylsulfamoyl-anilino)-acrylic acid ethyl ester

(E)-2-Cyano-3-(toluene-4-sulfonylamino)-acrylic acid ethyl ester

3-(5-benzyl-[1,2,4]oxadiazol-3-ylamino)-2-cyano-acrylic acid ethyl ester

Refernces

• 1、 Angelaud, Remy,Burkhard, Johannes,Gosselin, Francis,Lao, David,Marx, Andreas,Ochsenbein, Miriam,Ranjan, Rohit,Stumpf, Andreas,Xu, Di. "Efficient, Protecting Group Free Kilogram-Scale Synthesis of the JAK1 Inhibitor GDC-4379". . p. 2537 - 2550. Retrieved 2021/11/24.
• 2、 -. "ANDROGEN RECEPTOR ANTAGONISTS". Paragraph 0534-0536. . Retrieved 2019/08/26.