Ethyl 2,2-diethylacetoacetate

Base Information

• Chemical Name: Ethyl 2,2-diethylacetoacetate
• CAS No.: 1619-57-4
• Molecular Formula: C10H18 O3
• Molecular Weight: 186.251
• Hs Code.: 2918300090
• European Community (EC) Number: 216-581-0
• DSSTox Substance ID: DTXSID60167269
• Nikkaji Number: J99.529K
• Wikidata: Q83036603
• Mol file: 1619-57-4.mol

Synonyms:Ethyl 2,2-diethylacetoacetate;1619-57-4;Ethyl 2,2-diethyl-3-oxobutanoate;Diethyl acetoacetate;EINECS 216-581-0;Butanoic acid, 2,2-diethyl-3-oxo-, ethyl ester;AI3-11058;Acetoacetic acid, 2,2-diethyl-, ethyl ester;2-Ethyl-2-Acetylbutyric Acid Ethyl Ester;SCHEMBL1728132;DTXSID60167269;BAA61957;ETHYL2,2-DIETHYLACETOACETATE;MFCD00048552;Ethyl 2,2-diethyl-3-oxobutanoate #;AKOS022181635;2,2-Diethylacetoacetic acid ethyl ester;2,2-diethyl-3-oxo-butyric acid ethyl ester;CS-0258182;FT-0609223;2,2-diethyl-3-oxo-butanoic acid ethyl ester;EN300-69330;Z1101445537

Chemical Property of Ethyl 2,2-diethylacetoacetate

Chemical Property:

• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: 1.4330
• Boiling Point: 213.5°Cat760mmHg
• Flash Point: 81.4°C
• PSA: 43.37000
• Density: 0.958g/cm³
• LogP: 1.94490
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 186.125594432
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

98% ^*data from raw suppliers

Ethyl2,2-Diethylacetoacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)(C(=O)C)C(=O)OCC
• Uses: Ethyl 2,2-Diethylacetoacetate is a useful reactant in organic synthesis.

Technology Process of Ethyl 2,2-diethylacetoacetate

There total 23 articles about Ethyl 2,2-diethylacetoacetate 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: 85.0%

ethyl bromide (74-96-4) + ethyl acetoacetate (141-97-9) → ethyl 2,2-diethyl-3-oxobutanoate (1619-57-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.03.036

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

Reference yield: 53.0%

ethyl bromide (74-96-4) + ethyl acetoacetate (141-97-9) → ethyl 3-ethoxy-2-butenoate (998-91-4) + ethyl 2,2-diethyl-3-oxobutanoate (1619-57-4) + ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

With aluminum oxide; sodium ethanolate; Yields of byproduct given. Title compound not separated from byproducts; 2.) room temperature, 5 d;

upstream raw materials:

ethyl bromide

ethyl acetoacetate

2-ethyl-3-oxo-butyric acid ethyl ester; sodium enolate

ethyl iodide

Downstream raw materials:

3-Hydroxy-3-methyl-2,2-diaethyl-5-phenyl-pentin-⁽⁴⁾-saeure-⁽¹⁾-aethylester

3,3-diethyl-2,4(1H,3H)-pyridinedione

3,3-diethyl-piperidine-2,4-dione

ethyl acetate

Refernces

• 1、 Sarthou, P.,Bram, G.,Guibe, F.,Corset, J.. "INFLUENCE DE LA SOLVATATION PAR LE TERT-BUTANOL SUR LA STRUCTURE ET LA REACTIVE DE L'ENOLATE DE POTASSIUM DE L'ACETYLACETATE D'ETHYLE EN PRESENCE DE COURONNE OU DE CRYPTAND. ETUDE PAR SPECTROMETRIE INFRA-ROUGE ET CINETIQE.". . p. 1043 - 1050. Retrieved 1980.
• 2、 Kurz et al.. "-". . p. 3679. Retrieved 1968.
• 3、 Halder, Joydev,Das, Debabrata,Nanda, Samik. "Enantioselective biocatalytic reduction of 2,2-disubstituted ethylacetoacetates: An indirect desymmetrization approach for the synthesis of enantiopure (S)-4-hydroxy-3,3-disubstituted pentane-2-ones". . p. 1197 - 1208. Retrieved 2015/10/28.
• 4、 Arumugam, Subramaniam,McLeod, Dale,Verkade, John G.. "Use of the Nonionic Superbase P(MeNCH2CH2)3N in the Selective Monoalkylation of Active-Methylene Compounds". . p. 3677 - 3679. Retrieved 2007/10/03.