Ethyl 4-chloroacetoacetate

Base Information

• Chemical Name: Ethyl 4-chloroacetoacetate
• CAS No.: 638-07-3
• Molecular Formula: C6H9ClO3
• Molecular Weight: 164.589
• Hs Code.: 29183000
• European Community (EC) Number: 211-317-0
• UNII: 5AE82250CM
• DSSTox Substance ID: DTXSID4044454
• Nikkaji Number: J24.754E
• Wikidata: Q15632787
• ChEMBL ID: CHEMBL3187729
• Mol file: 638-07-3.mol

Synonyms:COBE cpd;ECA cpd;ethyl 4-chloro-3-oxobutanoate;ethyl 4-chloroacetoacetate

Chemical Property of Ethyl 4-chloroacetoacetate

Chemical Property:

• Appearance/Colour: Colorless to pale reddish-yellow clear liquid
• Vapor Pressure: 2.87E-05mmHg at 25°C
• Melting Point: -8 °C
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 235.5 °C at 760 mmHg
• PKA: 9.56±0.46(Predicted)
• Flash Point: 96.7 °C
• PSA: 43.37000
• Density: 1.179 g/cm³
• LogP: 0.74750
• Storage Temp.: 2-8°C
• Solubility.: 47.0g/l
• Water Solubility.: 47.5 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 164.0240218
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 4-chloroacetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, C
• Hazard Codes: T,N,C
• Statements: 25-34-51/53-24/25-36
• Safety Statements: 26-36-45-61-36/37/39-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)CCl
• Uses: Ethyl-4-chloracetoacetate (CAAEt) is used as intermediate for organic syntheses, e.g. ethyl 4-chloro-3-arylaminocrotonates, diethyl succinylsuccinate, 2-alkyl-4-hydroxy-6-chloromethylpyrimidines, 4- chloromethylcoumarines. Product Data Sheet Ethyl 4-chloroacetoacetate is used as a precursor in the preparation of phosphorous ylides. It finds application in regular film coating, pharmaceutical coating and formulation.

Technology Process of Ethyl 4-chloroacetoacetate

There total 10 articles about Ethyl 4-chloroacetoacetate 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: 100.0%

ethyl acetoacetate (141-97-9) → ethyl (2-chloroaceto)acetate (638-07-3)

Guidance literature:

ethyl acetoacetate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at 0 ℃; for 1h; Inert atmosphere;

With methyl chlorosulfate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2018.02.036

Reference yield: 98.7%

ethyl acetate (141-78-6) + chloroacetic acid ethyl ester (105-39-5) → ethyl (2-chloroaceto)acetate (638-07-3)

Guidance literature:

In ethanol; dimethyl sulfoxide; at 128 - 152 ℃; for 22h; under 3648.24 - 6840.46 Torr; Temperature; Pressure; Inert atmosphere;

Reference yield: 97.3%

ethyl acetate (141-78-6) + methyl chloroacetate (96-34-4) → ethyl (2-chloroaceto)acetate (638-07-3)

Guidance literature:

In methanol; N,N-dimethyl-formamide; at 110 - 145 ℃; for 15h; under 2280.15 - 6080.41 Torr; Inert atmosphere;

upstream raw materials:

n-hexan-2-one

4,4-dichloro-3-oxobutyric acid ethyl ester

benzaldehyde

4-chloroacetoacetyl chloride

Downstream raw materials:

2-chloroacetyl-3-phenyl-acrylic acid ethyl ester

ethyl (2-methyl-1,3-thiazol-4-yl)acetate

ethyl 4-hydroxy-1,2-oxazole-3-carboxylate

γ-(3,4,5-Trimethoxy-phenylmercapto)-acetessigethylester

Refernces

• 1、 -. "Continuous device and method for industrial production 4 - chloroacetoacetate". Paragraph 0024; 0040-0041; 0042-0043; 0044-0045; 0046-0047. . Retrieved 2021/11/06.
• 2、 -. "Method for synthesizing oxiracetam intermediate 4-ethyl chloroacetoacetate". Paragraph 0029-0034; 0041-0046; 0047-0054. . Retrieved 2019/03/28.