Methyl 2-ethylacetoacetate

Base Information

• Chemical Name: Methyl 2-ethylacetoacetate
• CAS No.: 51756-08-2
• Deprecated CAS: 123325-70-2
• Molecular Formula: C7H12 O3
• Molecular Weight: 144.17
• Hs Code.: 2918300090
• European Community (EC) Number: 257-381-3
• DSSTox Substance ID: DTXSID00871398
• Nikkaji Number: J113.160E
• Mol file: 51756-08-2.mol

Synonyms:Methyl 2-ethylacetoacetate;51756-08-2;Methyl 2-ethyl-3-oxobutanoate;Butanoic acid, 2-ethyl-3-oxo-, methyl ester;methyl-2-ethylacetoacetate;2-Ethyl-3-oxobutanoic acid, methyl ester;EINECS 257-381-3;methyl acetylbutyrate;methyl 2-acetylbutyrate;methyl 2 - ethylacetoacetate;Methyl2-ethyl-3-oxobutanoate;Methyl 2-ethyl-3-oxobutyrate;SCHEMBL222338;methyl 2-ethyl-3-oxo-butyrate;DTXSID00871398;Methyl 2-ethyl-3-oxobutanoate #;2-Acetylbutanoic acid methyl ester;BCA75608;MFCD01632136;AKOS000121358;AKOS017278456;FT-0695098;EN300-21229;Methyl 2-ethylacetoacetate, >=97.0% (GC);A828758;F0001-1348

Chemical Property of Methyl 2-ethylacetoacetate

Chemical Property:

• Vapor Pressure: 0.828mmHg at 25°C
• Refractive Index: n20/D 1.423
• Boiling Point: 262.4°Cat760mmHg
• PKA: 12.00±0.46(Predicted)
• Flash Point: 96.1°C
• PSA: 43.37000
• Density: g/cm³
• LogP: 0.77460
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 2-ethylacetoacetate ≥97.0% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)C)C(=O)OC

Technology Process of Methyl 2-ethylacetoacetate

There total 11 articles about Methyl 2-ethylacetoacetate 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: 93.1%

ethyl iodide (75-03-6) + acetoacetic acid methyl ester (105-45-3) → methyl 2-ethyl-3-oxobutanoate (51756-08-2)

Guidance literature:

With sodium methylate; In methanol; at -10 - 10 ℃; for 2h; Inert atmosphere;

Reference yield: 71.0%

ethyl bromide (74-96-4) + acetoacetic acid methyl ester (105-45-3) → methyl 2-ethyl-3-oxobutanoate (51756-08-2)

Guidance literature:

acetoacetic acid methyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 23 ℃; for 0.5h; Inert atmosphere;

ethyl bromide; In tetrahydrofuran; mineral oil; at 60 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201611845

Reference yield:

acetoacetic acid methyl ester (105-45-3) → methyl 2-ethyl-3-oxobutanoate (51756-08-2) + 2,2-diethyl-acetoacetic acid methyl ester (85153-63-5)

Guidance literature:

With C₃₃H₃₁NP₂Pd⁽²⁺⁾*2F₆Sb⁽¹⁺⁾; In nitromethane-d3; at 70 ℃; for 24h; under 750.075 Torr; Autoclave;

DOI:10.1021/om1006787

upstream raw materials:

methanol

sodium methylate

ethyl acetoacetate

2-acetoacetic acid

Downstream raw materials:

Benzoic acid 1-ethyl-1-methoxycarbonyl-2-oxo-propyl ester

2-acetyl-3-methylindole

Benzoic acid (R)-1-ethyl-1-methoxycarbonyl-2-oxo-propyl ester

2-ethyl-1-butanol

Refernces

• 1、 Arredondo, Vanessa,Hiew, Stanley C.,Gutman, Eugene S.,Premachandra, Ilandari Dewage Udara Anulal,Van Vranken, David L.. "Enantioselective Palladium-Catalyzed Carbene Insertion into the N?H Bonds of Aromatic Heterocycles". supporting information. p. 4156 - 4159. Retrieved 2017/04/03.
• 2、 Chen, Weijie,Seidel, Daniel. "Redox-Annulation of Cyclic Amines and β-Ketoaldehydes". supporting information. p. 1024 - 1027. Retrieved 2016/03/15.