Ethyl 2-chloroacetoacetate

Base Information

• Chemical Name: Ethyl 2-chloroacetoacetate
• CAS No.: 609-15-4
• Deprecated CAS: 121181-21-3,150010-45-0,150010-45-0
• Molecular Formula: C6H9ClO3
• Molecular Weight: 164.589
• Hs Code.: 29183000
• European Community (EC) Number: 210-180-4
• NSC Number: 78426
• UNII: A9GFN94N9A
• DSSTox Substance ID: DTXSID3049330
• Nikkaji Number: J60.802E
• ChEMBL ID: CHEMBL3186400
• Mol file: 609-15-4.mol

Synonyms:A 21960;A-21960

Chemical Property of Ethyl 2-chloroacetoacetate

Chemical Property:

• Appearance/Colour: clear bright yellow liquid
• Vapor Pressure: 0.086mmHg at 25°C
• Melting Point: -80 °C
• Refractive Index: n20/D 1.441(lit.)
• Boiling Point: 225.5 °C at 760 mmHg
• PKA: 7.92±0.46(Predicted)
• Flash Point: 50 °C
• PSA: 43.37000
• Density: 1.176 g/cm³
• LogP: 0.74590
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: 17 g/L (20 ºC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 164.0240218
• Heavy Atom Count: 10
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2-Chloracetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xn, F
• Hazard Codes: C,Xn,F
• Statements: 10-22-34-52/53-36/37/38-36
• Safety Statements: 16-26-36/37/39-45-61-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CCOC(=O)C(C(=O)C)Cl
• Uses: Ethyl 2-chloroacetoacetate was used to study reductive dechlorination of β-keto ester ethyl 2-chloroacetoacetate by Saccharomyces cerevisiae.

Technology Process of Ethyl 2-chloroacetoacetate

There total 26 articles about Ethyl 2-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-chloro-3-oxo-butyrate (609-15-4)

Guidance literature:

With thionyl chloride; In tetrachloromethane; at 20 ℃; for 1h;

DOI:10.1002/jhet.2302

Reference yield: 97.0%

ethyl acetoacetate (141-97-9) → ethyl 2,2-dichloroacetoacetate (6134-66-3) + ethyl 2,2,4-trichloro-3-oxobutyrate (85153-67-9) + ethyl 2-chloro-3-oxo-butyrate (609-15-4)

Guidance literature:

With chlorine; at 55 - 60 ℃; for 9h; Product distribution; Mechanism; dinamics of chlorination of acetoacetic ester, products in the mixture on the time;

Reference yield: 46.0%

ethyl 3-oxobutanate sodium salt (20412-62-8,66279-49-0) → ethyl 2-chloro-3-oxo-butyrate (609-15-4)

Guidance literature:

With tetrachloromethane; In dimethyl sulfoxide; for 16h; Heating; at 20 - 25 deg C in different bipolar aprotic solvents;

upstream raw materials:

4-methyleneoxetan-2-one

ethanol

chloroform

acetic acid-(2,4,N-trichloro-anilide)

Downstream raw materials:

6-chloro-5-methyl-4H-[1,2,4]triazolo[1,5-a]pyrimidin-7-one

3-benzylidenehydrazino-5-methyl-1⁽²⁾H-pyrazole-4-carboxylic acid ethyl ester

4-(2-hydroxy-acetoacetylamino)-benzoic acid

ethyl 4-methylthiazole-5-carboxylate

Refernces

Discovery of orally active pyrazoloquinolines as potent PDE10 inhibitors for the management of schizophrenia

10.1016/j.bmcl.2011.11.023

The research aims to develop new treatments for schizophrenia by identifying potent and selective PDE10 inhibitors. Schizophrenia is a mental illness affecting about 1% of the world's population, and current treatments are often ineffective against negative symptoms and cognitive disorders, while also causing adverse effects. PDE10, a dual cAMP/cGMP phosphodiesterase, is highly expressed in the striatal medium spiny neurons and its inhibition can mimic D2 dopamine receptor antagonism, potentially normalizing the reduced striatal output characteristic of schizophrenia. The researchers synthesized a series of pyrazoloquinoline analogs and optimized their chemical properties through structure-activity relationship (SAR) studies. Key chemicals used in the research include aniline, phenyl isothiocyanate, ethyl 2-chloroacetoacetate, and various heterocyclic amines. The study identified several highly potent and selective PDE10 inhibitors, such as compounds 16 and 27, which demonstrated significant oral antipsychotic activity in the MK-801 induced hyperactive rat model. The research concludes that these pyrazoloquinoline-based PDE10 inhibitors hold promise as novel therapeutic agents for schizophrenia, with compound 27 showing particularly favorable pharmacokinetic properties and safety profiles.

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