Ethyl 2,3-butadienoate

Base Information

• Chemical Name: Ethyl 2,3-butadienoate
• CAS No.: 14369-81-4
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• Hs Code.: 29161900
• European Community (EC) Number: 627-301-5
• DSSTox Substance ID: DTXSID60398955
• Nikkaji Number: J563.545D
• ChEMBL ID: CHEMBL4078403
• Mol file: 14369-81-4.mol

Synonyms:ethyl 2,3-butadienoate

Chemical Property of Ethyl 2,3-butadienoate

Chemical Property:

• Vapor Pressure: 7.36mmHg at 25°C
• Refractive Index: n20/D 1.46(lit.)
• Boiling Point: 136.5 °C at 760 mmHg
• Flash Point: 47.8 °C
• PSA: 26.30000
• Density: 0.898 g/cm³
• LogP: 0.89060
• Storage Temp.: <0°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 121

Purity/Quality:

99%, ^*data from raw suppliers

Ethylbuta-2,3-dienoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C=C
• Uses: Ethyl Buta-2,3-dienoate is a useful reactant for the synthesis of 9H-?pyrrolo[1,?2-?a]?indole derivatives via a phosphine-?promoted Michael addn.?/intramol. Wittig reaction. Ethyl 2,3-butadienoate may be used in the synthesis of dihydropyrans by reacting with acyclic enones. It may also be used to synthesize spiranic heterocycles by reacting with heterocyclic bis-arylidene ketones via phosphine-catalyzed [3+2] annulations.

Technology Process of Ethyl 2,3-butadienoate

There total 17 articles about Ethyl 2,3-butadienoate 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%

ethyl cyanoacetate (53841-07-9) → ethyl 2,3-butadienoate (14369-81-4)

Guidance literature:

With potassium carbonate;

DOI:10.1007/BF01168281

Reference yield: 92.0%

acetyl chloride (75-36-5) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 2,3-butadienoate (14369-81-4)

Guidance literature:

ethyl (triphenylphosphoranylidene)acetate; With triethylamine; In dichloromethane; for 0.166667h;

acetyl chloride; In dichloromethane; for 0.833333h;

DOI:10.1016/j.tet.2016.07.075

Reference yield: 78.0%

→ ethyl 2,3-butadienoate (14369-81-4)

Guidance literature:

With carbon monoxide; In benzene-d6; at 62 ℃;

DOI:10.1021/ja00229a025

upstream raw materials:

ethanol

2-propynyl chloride

acetic acid

ethyl cyanoacetate

Downstream raw materials:

3-phenylaminobut-2-enoic acid ethyl ester

ethyl 3-((4-ethoxyphenyl)amino)but-2-enoate

ethyl 3-(phenylsulfonyl)but-3-enoate

ethyl-2,5-dimethyl-3-phenylisoxazolidine-4-carbonitrile

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