Ethyl diacetoacetate

Base Information

• Chemical Name: Ethyl diacetoacetate
• CAS No.: 603-69-0
• Molecular Formula: C8H12O4
• Molecular Weight: 172.181
• Hs Code.: 29183000
• European Community (EC) Number: 210-053-3
• NSC Number: 345
• UNII: K6CX8BFF7J
• DSSTox Substance ID: DTXSID80209059
• Nikkaji Number: J6.811J
• Wikidata: Q72474133
• Mol file: 603-69-0.mol

Synonyms:Ethyl diacetoacetate;603-69-0;Ethyl 2-acetyl-3-oxobutanoate;Ethyl 2-acetylacetoacetate;Ethyl diacetylacetate;Butanoic acid, 2-acetyl-3-oxo-, ethyl ester;Ethyl diacetyl acetate;K6CX8BFF7J;Acetoacetic acid, 2-acetyl-, ethyl ester;NSC-345;EINECS 210-053-3;2-acetyl-3-oxobutyric acid ethyl ester;2-acetyl-3-oxo-butyric acid ethyl ester;ethyl diacetyl-acetate;UNII-K6CX8BFF7J;ethyl 2-acetyl-acetoacetate;Ethyl diacetoacetate, 97%;Diacetylessigsaure-athylester;Ethyl2-acetyl-3-oxobutanoate;SCHEMBL123766;Diacetoacetic Acid Ethyl Ester;Ethyl 2-Acetyl-3-oxobutyrate;ethyl 2-acetyl-3-oxo-butyrate;NSC345;DTXSID80209059;NSC 345;2-Acetyl-3-oxobutyric acid ethyl;Ethyl 2-acetyl-3-oxobutanoate #;STR02893;MFCD00009864;STL170045;AKOS004115440;CS-W001121;2-Acetyl-3-oxobutanoic acid ethyl ester;A8423;D2170;FT-0610967;EN300-49187;D77633;W-105256;F0001-1581

Chemical Property of Ethyl diacetoacetate

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 8.24E-06mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• Boiling Point: 210 °C at 760 mmHg
• PKA: 6.93±0.46(Predicted)
• Flash Point: 85 °C
• PSA: 60.44000
• Density: 1.085 g/cm³
• LogP: 0.34370
• Water Solubility.: Not miscible in water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Ethyl Diacetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(=O)C)C(=O)C
• Uses: Ethyl diacetoacetate is used in the preparation of 3-acetyl-6-chloro-7-hydroxy-4-methylcoumarin. It is used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of Ethyl diacetoacetate

There total 44 articles about Ethyl diacetoacetate 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: 91.0%

ethyl acetoacetate (141-97-9) + acetyl chloride (75-36-5) → ethyl 2-acetylacetoacetate (603-69-0)

Guidance literature:

ethyl acetoacetate; With ethanol; magnesium; In tetrachloromethane; toluene; for 1h; Heating;

acetyl chloride; In tetrachloromethane; toluene; at 0 - 20 ℃; for 1.5h;

DOI:10.3987/COM-04-10216

Reference yield: 70.3%

1-Chloro-1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-6-iodo-hexane (16486-97-8) → 1-chloro-1H,6H-dodecafluoro-hexane (307-22-2) + (E)-3-(5-Chloro-1,1,2,2,3,3,4,4,5,5-decafluoro-pentyl)-pent-2-enedioic acid diethyl ester + ethyl 2-acetylacetoacetate (603-69-0)

Guidance literature:

With sodium; ethyl acetoacetate; In ethanol; N,N-dimethyl-formamide; at 75 ℃; for 10h;

DOI:10.1016/S0022-1139(00)85017-4

Reference yield: 22.1%

1-Chloro-1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-6-iodo-hexane (16486-97-8) + ethyl acetoacetate (141-97-9) → 1-chloro-1H,6H-dodecafluoro-hexane (307-22-2) + (E)-3-(5-Chloro-1,1,2,2,3,3,4,4,5,5-decafluoro-pentyl)-pent-2-enedioic acid diethyl ester + ethyl 2-acetylacetoacetate (603-69-0)

Guidance literature:

With sodium; In ethanol; N,N-dimethyl-formamide; at 75 ℃; for 10h;

DOI:10.1016/S0022-1139(00)85017-4

upstream raw materials:

3-acetoxy-crotonic acid ethyl ester

acetic anhydride

ethyl acetoacetate

sodium ethyl acetylacetate enolate

Downstream raw materials:

4-hydroxy 2,6-dimethylpyrimidine

1-(3-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester

3,5-dimethyl-1-m-tolyl-1H-pyrazole-4-carboxylic acid ethyl ester

ethyl 1-(4-tolyl)-3,5-dimethylpyrazole-4-carboxylate

Refernces

• 1、 Elion. "-". . p. 248. Retrieved .
• 2、 Jung, Jae-Chul,Blake Watkins,Avery, Mitchell A.. "Synthesis and cyclization reaction of pyrazolin-5-one derivatives". . p. 77 - 94. Retrieved 2007/10/03.
• 3、 Bingham,Tyman. "Improved synthesis of alkyl diacetylacetates". . p. 357 - 361. Retrieved 2007/10/03.