ethyl (E)-2-cyano-3-methylpent-2-enoate

Base Information

• Chemical Name: ethyl (E)-2-cyano-3-methylpent-2-enoate
• CAS No.: 759-51-3
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.208
• European Community (EC) Number: 212-069-6
• NSC Number: 67978
• Nikkaji Number: J191.626B
• Mol file: 759-51-3.mol

Synonyms:759-51-3;ethyl (E)-2-cyano-3-methylpent-2-enoate;(E/Z)-2-Cyano-3-methyl-2-pentenoic Acid Ethyl Ester;Ethyl 2-cyano-3-methylpent-2-ene-1-oate;EINECS 212-069-6;AI3-04908;(E/Z)-2-Cyano-3-methyl-2-pentenoicAcidEthylEster-d3;2-CYANO-3-METHYL-PENT-2-ENOIC ACID ETHYL ESTER;NSC67978;ethyl (2E)-2-cyano-3-methyl-2-pentenoate;ethyl (2E)-2-cyano-3-methylpent-2-enoate;SCHEMBL6052436;SCHEMBL8277427;NSC 67978;NSC-67978;AKOS024332487;ethyl (E)-2-cyano-3-methyl-pent-2-enoate;ETHYL 2-CYANO-3-METHYL-2-PENTENOATE;2-Cyano-3-methyl-2-pentenoic acid ethyl ester;A838561;(E)-2-cyano-3-methyl-2-pentenoic acid ethyl ester;2-Pentenoic acid, 2-cyano-3-methyl-, ethyl ester

Chemical Property of ethyl (E)-2-cyano-3-methylpent-2-enoate

Chemical Property:

• Vapor Pressure: 0.0155mmHg at 25°C
• Boiling Point: 256.3°C at 760 mmHg
• Flash Point: 113.8°C
• PSA: 50.09000
• Density: 1g/cm³
• LogP: 1.79958
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 167.094628657
• Heavy Atom Count: 12
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

(E/Z)-2-Cyano-3-methyl-2-pentenoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C(C#N)C(=O)OCC)C
• Isomeric SMILES: CC/C(=C(\C#N)/C(=O)OCC)/C
• Uses: Intermediate in the preparation of Ethosuximide.

Technology Process of ethyl (E)-2-cyano-3-methylpent-2-enoate

There total 3 articles about ethyl (E)-2-cyano-3-methylpent-2-enoate 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: 99.0%

ethyl 2-cyanoacetate (105-56-6) + butanone (78-93-3) → 2-cyano-3-methyl-pent-2-enoic acid ethyl ester (759-51-3,25528-06-7,53246-72-3)

Guidance literature:

piperidine; at 23 ℃; for 2h; under 2250180 Torr;

DOI:10.1016/S0040-4039(00)01930-4

Reference yield: 20.0%

C7H16N4 (125256-49-7) + ethyl (2Z)-2-cyano-3-ethoxypent-2-enoate (25468-53-5) → 2-cyano-3-methyl-pent-2-enoic acid ethyl ester (759-51-3,25528-06-7,53246-72-3) + 1-amino-4-ethyl-2-dimethylamino-6-oxo-1,6-dihydropyrimidine-5-carbonitrile + butanone N(3)-[(2-cyano-2-ethoxycarbonyl-1-ethyl)vinyl]amino-N(4),N(4)-dimethylaminomethylenehydrazone + 2-Dimethylamino-4-ethyl-6-imino-1-[1-methyl-prop-(E)-ylideneamino]-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

Guidance literature:

In benzene; for 20h; Ambient temperature;

DOI:10.1002/jhet.5570330447

Reference yield:

→ 2-cyano-3-methyl-pent-2-enoic acid ethyl ester (759-51-3,25528-06-7,53246-72-3)

Guidance literature:

Methode Cope;

upstream raw materials:

ethyl 2-cyanoacetate

butanone

C₇H₁₆N₄

ethyl (2Z)-2-cyano-3-ethoxypent-2-enoate

Downstream raw materials:

malonic acid

3-benzyl-2-cyano-3-methyl-valeric acid ethyl ester

cyanoacetic acid

ethyl 2-cyano-3-methylvalerate

Refernces

• 1、 Zhou, Shuai,Liu, Lu,Wang, Bo,Ma, Mingguo,Xu, Feng,Sun, Runcang. "Novel basic ionic liquid based on alkylammonium as efficient catalyst for Knoevenagel reaction". experimental part. p. 1384 - 1391. Retrieved 2012/04/10.
• 2、 Miyamoto, Yoshiko,Yamazaki, Chiji. "Synthesis of nitrogen-containing heterocycles. 7 reaction of aliphatic diaminomethylenehydrazones with hindered ethoxymethylenecyanoacetate". . p. 1285 - 1289. Retrieved 2007/10/03.