Encyclopedia / Pharmaceutical Intermediates / Organic Intermediates / Organic Intermediate

Ethyl diacetoacetate

CAS：603-69-0
MW:172.18
MF：C8H12O4

Ethyl diacetoacetate, with the chemical formula C8H12O5 and CAS registry number 603-69-0, is a compound known for its applications in organic synthesis. This colorless liquid, also referred to as ethyl acetoacetate diethyl ester, is characterized by its acetoacetate functional group. It is commonly used as a versatile building block in the production of pharmaceuticals, agrochemicals, and dyes. Ethyl diacetoacetate serves as a precursor for the synthesis of various compounds, including β-ketoesters, pyrazoles, and pyrimidines. It can undergo condensation reactions to form β-diketones, which are important intermediates in the synthesis of heterocyclic compounds. Ethyl diacetoacetate is also used as a flavoring agent in the food industry. Overall, this compound plays a crucial role in the development of diverse chemical processes and products.

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

1. Names and Identifiers

1.1 Name: Ethyl diacetoacetate

1.2 Synonyms: 2-acetyl-3-oxo-butyric acid ethyl ester; 3-carboethoxy-2,4-pentanedione; 3-ETHOXYCARBONYLACETYLACETONE; 3-ethoxycarbonylpentane-2,4-dione; Acetoacetic acid, 2-acetyl-, ethyl ester; Butanoic acid, 2-acetyl-3-oxo-, ethyl ester; DIACETOACETIC ACID ETHYL ESTER; Diethyl diacetoacetate; EINECS 210-053-3; Ethyl 2-acetyl-3-oxobutanoate; ETHYL 2-ACETYL-3-OXOBUTYRATE; Ethyl 2-acetylacetoacetate; ethyl acetylacetoacetate; ETHYL DIACETYL ACETATE; Ethyldiacetoacetate; MFCD00009864;

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1.3 CAS No.: 603-69-0

1.4 CID: 79063

1.5 EINECS: 210-053-3

1.6 Molecular Formula: C8H12O4

1.7 Inchi: InChI=1S/C8H12O4/c1-4-12-8(11)7(5(2)9)6(3)10/h7H,4H2,1-3H3

1.8 InChkey: YMCDYRGMTRCAPZ-UHFFFAOYSA-N

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

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

2. Properties

2.1 Appearance: clear colorless to yellow liquid

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: clear colorless to yellow liquid Ethyl diacetoacetate Preparation Products And Raw materials Preparation Products

2.4 pKa: 6.93±0.46(Predicted)

2.5 Water Solubility: Not miscible in water.

3. Use and Manufacturing

3.1 Description

Ethyl diacetoacetate, with the chemical formula C8H12O5, has the CAS number 603-69-0. It is a colorless liquid with a fruity odor. The basic structure of ethyl diacetoacetate consists of an ethyl group attached to two acetoacetate groups. This compound is soluble in organic solvents such as ethanol and acetone, but it is sparingly soluble in water. Ethyl diacetoacetate should be handled with care as it may cause irritation to the skin, eyes, and respiratory system. It is also flammable and should be kept away from heat, sparks, and open flames. In case of ingestion or inhalation, immediate medical attention should be sought. Ethyl diacetoacetate is not considered to be a significant environmental hazard.

Applicable Fields

Pharmaceuticals: Ethyl diacetoacetate is commonly used as a building block in the synthesis of various pharmaceutical compounds. Its mechanism of action in this field involves its ability to undergo reactions such as condensation, esterification, and alkylation, which are essential in the production of pharmaceutical intermediates and active pharmaceutical ingredients.

Flavor and Fragrance: This compound is also used in the flavor and fragrance industry. It imparts a fruity and sweet aroma to products such as perfumes, soaps, and food flavorings. The mechanism of action in this context is based on its ability to interact with odor receptors in the nose, resulting in the perception of a specific scent or taste.

Storage

Conditions: Store in a cool and dry place.

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4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. 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 : Predict

Predict 1H proton NMR

IR : liquid film

Mass

Mass spectrum (electron ionization)

6. Synthesis Route

603-69-0Total: 28 Synthesis Route

75-36-5 218 Suppliers

603-69-0 34 Suppliers

141-97-9 355 Suppliers

603-69-0 34 Suppliers

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7. Precursor and Product

precursor:

64-17-5

1007476-32-5

98-88-4

75-36-5

6287-35-0

141-97-9

29214-62-8

15435-71-9

product:

4786-61-2

61226-19-5

2199-44-2

18417-40-8

123-54-6

17147-42-1

5408-10-6

73773-25-8

113808-86-9

35691-93-1

8. Computed Properties

Molecular Weight：172.18g/mol
Molecular Formula：C₈H₁₂O₄
Compound Is Canonicalized：True
Exact Mass：0.3
XLogP3-AA：172.07355886
Monoisotopic Mass：172.07355886
Complexity：193
Rotatable Bond Count：5
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：4
Topological Polar Surface Area：60.4
Heavy Atom Count：：12
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAADQSggAICCAAABAAIAICQCAAAAAAAAAAAAAEAAAAAABYIAAACAAAEIAAAAAAAAAAKAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9.Other Information

Usage: 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.

BRN: 775014

Chemical Properties: clear colorless to yellow liquid

General Description: Ethyl diacetoacetate reacts with o-phenylenediamine to yield 2-methylbenzimidazole perchlorate.

10. Toltal 31 Suppliers View more

Dayang Chem (Hangzhou) Co., Ltd.

^1YR

Tel: Update Time:2024/06/17

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XinChem Corporation

Tel: Update Time:2019/11/25

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AOPHARM

Tel: Update Time:2019/05/05

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Shanghai Hope Chem Co., Ltd.

Tel: Update Time:2018/11/21

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Pure Chemistry Scientific Inc.

Tel: Update Time:2019/02/25

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11. Realated Product Infomation