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Ethyl 2-chloroacetoacetate

CAS：609-15-4
MW:164.58686
MF：C6H9ClO3

Ethyl 2-chloroacetoacetate, with the chemical formula C6H9ClO3 and CAS registry number 609-15-4, is a compound known for its applications in organic synthesis. This colorless liquid, also referred to as ethyl chloroacetoacetate, is characterized by its chlorine and acetoacetate functional groups. It is commonly used as a reagent in the preparation of various organic compounds, including pharmaceutical intermediates and agrochemicals. Ethyl 2-chloroacetoacetate is known for its ability to undergo condensation reactions, making it a valuable building block in the synthesis of complex molecules. It is important to handle this compound with caution, as it is flammable and may cause irritation to the skin, eyes, and respiratory system. Overall, ethyl 2-chloroacetoacetate plays a crucial role in the field of organic chemistry, offering a versatile platform for the introduction of chlorine and acetoacetate moieties into different molecules.

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Names and ldentifier
Properties
Use and Manufacturing
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Ethyl 2-chloroacetoacetate

1.2 Synonyms: 2-Chloro-3-oxobutanoic acid ethyl ester; 2-chloro-3-oxo-butanoicaciethylester; 2-Chloro-3-oxobutyric acid ethyl ester; 2-Chloroacetoacetic Acid Ethyl Ester; A 21960; Acetoacetic acid, 2-chloro-, ethyl ester; Butanoic acid, 2-chloro-3-oxo-, ethyl ester; Butanoic acid, 2-chloro-3-oxo-, ethyl ester, (2R)-; Butanoic acid, 2-chloro-3-oxo-, ethyl ester, (2S)-; Ethyl (2R)-2-chloro-3-oxobutanoate; Ethyl (2S)-2-chloro-3-oxobutanoate; Ethyl 2-chloracetoacetate; Ethyl 2-chloro-3-oxobutanoate; Ethyl 2-chloro-3-oxobutyrate; ETHYL ALPHA-CHLOROACETOACETATE; Ethyl α-chloroacetoacetate; Ethyl α-chloroacetylacetate; NSC 78426; Oxiracetam Impurity 12;

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1.3 CAS No.: 609-15-4

1.4 CID: 11858

1.5 EINECS: 210-180-4

1.6 Molecular Formula: C6H9ClO3

1.7 Inchi: InChI=1S/C6H9ClO3/c1-3-10-6(9)5(7)4(2)8/h5H,3H2,1-2H3

1.8 InChkey: RDULEYWUGKOCMR-UHFFFAOYSA-N

1.9 Canonical Smiles: CCOC(=O)C(C(=O)C)Cl

1.10 Isomers Smiles: CCOC(=O)C(C(=O)C)Cl

2. Properties

2.1 Solubility: 17 g/L (20 ºC)

2.2 Appearance: Clear yellow Liquid

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: clear bright yellow liquid Ethyl 2-chloroacetoacetate Preparation Products And Raw materials Preparation Products

2.5 Color/Form: Clear yellow

2.6 pKa: 7.92±0.46(Predicted)

2.7 Water Solubility: H2O: 17 g/L (20 oC)

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

3. Use and Manufacturing

3.1 Description

Ethyl 2-chloroacetoacetate, with the chemical formula C6H9ClO3, has the CAS number 609-15-4. It is a chemical compound that appears as a colorless liquid with a fruity odor. The basic structure of Ethyl 2-chloroacetoacetate consists of an ethyl group attached to a carbon atom, which is further attached to a chlorine atom and two carbonyl groups. This compound is soluble in organic solvents but sparingly soluble in water. Safety information suggests that Ethyl 2-chloroacetoacetate may cause irritation to the skin and eyes, and it should be handled with care. It is important to avoid inhalation or ingestion of this chemical. Proper protective measures should be taken when working with Ethyl 2-chloroacetoacetate to ensure safety.

Applicable Fields

Pharmaceuticals: Ethyl 2-chloroacetoacetate is commonly used in the pharmaceutical industry as an intermediate in the synthesis of various compounds. Its purpose in this field involves its ability to undergo chemical reactions and form new compounds. The mechanism of action in pharmaceuticals involves the incorporation of Ethyl 2-chloroacetoacetate into the desired molecule, leading to the synthesis of specific pharmaceutical products.

Chemical Synthesis: This compound is also utilized in chemical synthesis for the production of other organic compounds. Its purpose in this field involves its reactivity and ability to participate in various chemical reactions. The mechanism of action in chemical synthesis involves the reaction of Ethyl 2-chloroacetoacetate with other reagents to form desired products.

Storage

Conditions: Store in a cool and dry place, away from direct sunlight.

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3.2 Methods of Manufacturing: The preparation method is to obtain α-chloroethyl acetoacetate by chlorination of ethyl acetoacetate. Equal molar ratio of ethyl acetoacetate and sulfuryl chloride are respectively dissolved in an appropriate amount of solvent, and the sulfuryl chloride solution is added dropwise to ethyl acetoacetate under low temperature, stirring and negative pressure, and then stirring is continued for several hours. The reactant was washed with saturated brine, and the water layer was separated. After the oil layer was dried with anhydrous magnesium sulfate, it was desolventized and distilled under reduced pressure. The distilled product at 96～99℃/4～4.7kPa was collected, which is α-chloro Ethyl acetoacetate. The chlorinating agent in this reaction can also be replaced by chlorine.

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4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Skin corrosion, Category 1A

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H314 Causes severe skin burns and eye damage H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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5. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : liquid film

Mass

Mass spectrum (electron ionization)

6. Synthesis Route

609-15-4Total: 20 Synthesis Route

141-97-9 355 Suppliers

609-15-4 148 Suppliers

141-97-9 355 Suppliers

88-00-6 1 Suppliers

609-15-4 148 Suppliers

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7. Precursor and Product

precursor:

104690-31-5

141-97-9

20412-62-8

60930-76-9

product:

6134-66-3

7238-62-2

617-35-6

2510-32-9

105-39-5

67271-32-3

4620-52-4

5405-41-4

1522-41-4

3885-38-9

8. Computed Properties

Molecular Weight：164.58686g/mol
Molecular Formula：C₆H₉ClO₃
Compound Is Canonicalized：True
Exact Mass：1.1
XLogP3-AA：164.0240218
Monoisotopic Mass：164.0240218
Complexity：144
Rotatable Bond Count：4
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：43.4
Heavy Atom Count：：10
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：1
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBgMAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgIAAAAACAeggEICCAAABAAIAICQCAAAAAAAAAAAAAEAAwBAABQIAAACAAAEIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9.Other Information

Mesh Entry Terms: A 21960

Manufacturing Info: Butanoic acid, 2-chloro-3-oxo-, ethyl ester: ACTIVE

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11. Related Questions

: How can Ethyl 2-chloroacetoacetate be prepared more efficiently?Ethyl 2-chloroacetoacetate is a widely used organic synthesis intermediate. It is a transparent liquid with a boiling point of 107-108℃/1.87kPa. However, the current process for separation and purifi..; How to prepare and use Ethyl 2-chloroacetoacetate effectively?Background and overview[1][2] Ethyl 2-chloroacetoacetate is an important intermediate in the synthesis of the drug febuxostat. Febuxostat is a new generation xanthine oxidase inhibitor developed by Te..

12. Realated Product Infomation