Ethyl 2-ethylacetoacetate

Base Information

• Chemical Name: Ethyl 2-ethylacetoacetate
• CAS No.: 607-97-6
• Deprecated CAS: 105139-93-3
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Hs Code.: 29183000
• European Community (EC) Number: 210-151-6
• NSC Number: 53775
• UNII: Y65CB79AQC
• DSSTox Substance ID: DTXSID40862285
• Nikkaji Number: J44.189I
• Mol file: 607-97-6.mol

Synonyms:Ethyl 2-ethylacetoacetate;607-97-6;Ethyl 2-ethyl-3-oxobutanoate;Ethyl 2-acetylbutyrate;Butanoic acid, 2-ethyl-3-oxo-, ethyl ester;2-Ethylacetoacetic Acid Ethyl Ester;Ethyl 2-ethyl-3-ketobutyrate;Ethyl alpha-acetylbutyrate;Ethyl alpha-ethylacetoacetate;Ethyl .alpha.-ethylacetoacetate;Acetoacetic acid, 2-ethyl-, ethyl ester;Ethyl ethyl acetoacetate;ethyl-2-ethylacetoacetate;MFCD00039898;NSC 53775;2-ethyl-3-oxo-butyric acid ethyl ester;Ethyl .alpha.-acetylbutyrate;ethyl 2-ethyl-3-oxobutyrate;EINECS 210-151-6;NSC-53775;2-Ethyl-3-oxobutanoic acid ethyl ester;AI3-06006;ethyl 2-ethyl-3-oxo-butanoate;Ethyl ethylacetoacetate;ethyl 2-acetylbutanoate;Ethyl2-Ethylacetoacetate;ethyl-2 ethylacetoacetate;ethyl 2-ethyl-acetoacetate;Y65CB79AQC;SCHEMBL856078;ethyl 2-ethyl-3-oxo-butyrate;Ethyl 2-ethyl-3-oxobutanoate #;Ethyl 2-ethylacetoacetate, 90%;2-Acetylbutyric Acid Ethyl Ester;2-Ethyl-3-oxobutyric acid ethyl;DTXSID40862285;ETHYL 2-ETHYLACETYLACETATE;NSC53775;STL185642;AKOS000120029;AKOS016042090;CS-W008164;AS-18443;SY021467;AM20100476;BB 0259255;E0895;FT-0612245;FT-0661179;EN300-19800;O11754;A832890;W-105229;F0001-1590;105139-93-3

Chemical Property of Ethyl 2-ethylacetoacetate

Chemical Property:

• Appearance/Colour: Colorless liquid.
• Vapor Pressure: 0.554mmHg at 25°C
• Melting Point: 170 °C (decomp)
• Refractive Index: n20/D 1.421(lit.)
• Boiling Point: 190 °C at 760 mmHg
• PKA: 12.02±0.46(Predicted)
• Flash Point: 75.7 °C
• PSA: 43.37000
• Density: 0.979 g/cm³
• LogP: 1.16470
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

95%,98%, ^*data from raw suppliers

Ethyl 2-Ethylacetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C(=O)C)C(=O)OCC
• Uses: Ethyl 2-ethylacetoacetate was used in the synthesis of 2-alkylidenetetrahydrofurans, diphenyllead(IV) thiosemicarbazonates and pyrazolonates. It was used as starting reagent in the synthesis of 2-ethylfumaric acid.

Technology Process of Ethyl 2-ethylacetoacetate

There total 55 articles about Ethyl 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: 94.9%

ethyl bromide (74-96-4) + ethyl acetoacetate (141-97-9) → ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

With sodium ethanolate; In ethanol; at -10 - 10 ℃; for 2h; Inert atmosphere;

Reference yield: 87.0%

ethyl acetoacetate (141-97-9) + ethyl iodide (75-03-6) → ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

With sodium; In tetrahydrofuran; for 20h; Heating;

DOI:10.1002/jhet.5570410603

Reference yield: 78.0%

ethyl acetoacetate (141-97-9) + ethyl iodide (75-03-6) → ethyl 2,2-diethyl-3-oxobutanoate (1619-57-4) + ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

With P(MeNCH₂CH₂)3N; In hexane; acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1021/jo972350i

upstream raw materials:

4-ethyl-3-methyl-pentenedioic acid diethyl ester

2-acetyl-3-methyl-succinic acid-1-ethyl ester

ethyl bromide

ethyl acetoacetate

Downstream raw materials:

5-ethyl-6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

4-ethyl-5-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one

ethyl 2,2-diethyl-3-oxobutanoate

3-ethyl-2,6-dimethyl-chromen-4-one

Refernces

• 1、 Nee, Gerard,Bottin-Strzalko, Tekla,Seyden-Penne, Jacqueline,Beaujean, Michel,Viehe, Heinz. "HMPA Dehydro Dimer: A Remarkable Complexing Agent of Lithium Cation". . p. 1111 - 1114. Retrieved 1983.
• 2、 Michael. "-". . p. 553. Retrieved .
• 3、 Kou, Xuezhen,Shao, Qihang,Ye, Chenghao,Yang, Guoqiang,Zhang, Wanbin. "Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary or Two Vicinal Stereocenters". supporting information. p. 7587 - 7597. Retrieved 2018/06/04.
• 4、 Sheng, Xuguang,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi. "Tunable Aerobic Oxidative Hydroxylation/Dehydrogenative Homocoupling of Pyrazol-5-ones under Transition-Metal-Free Conditions". supporting information. p. 2618 - 2621. Retrieved 2017/05/24.