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Isopropyl acetoacetate

CAS：542-08-5
MW:144.16838
MF：C7H12O3

Isopropyl acetoacetate, with the chemical formula C7H12O3 and CAS registry number 542-08-5, is a compound known for its applications in various chemical processes. This colorless liquid, also referred to as acetoacetic acid isopropyl ester, is characterized by its acetoacetate functional group. It is commonly used as a reagent in organic synthesis, offering a versatile platform for the introduction of acetoacetate moieties into different molecules. Isopropyl acetoacetate is often used in the production of pharmaceuticals, agrochemicals, and other fine chemicals. It can also be used as a solvent and a flavoring agent. Isopropyl acetoacetate is stable under normal conditions and should be stored in a cool, dry place. It is important to handle this compound with care as it may be harmful if swallowed, inhaled, or in contact with skin. Always follow proper safety precautions when working with Isopropyl acetoacetate.

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

1. Names and Identifiers

1.1 Name: Isopropyl acetoacetate

1.2 Synonyms: 3-Oxobutanoic acid 1-methylethyl ester; 3-Oxobutanoic acid isopropyl ester; 3-oxobutanoic acid propan-2-yl ester; 3-oxo-butanoicaci1-methylethylester; 3-Oxobutansαure-1-methylethylester; 3-Oxobutyric Acid Isopropyl Ester; 3-Oxo-butyricacidisopropylester; Acetoacetic Acid Isopropyl Ester; Acetoacetic acid, isopropyl ester; Acetoaceticacid,isopropylester; acetoaceticacidisopropylester; Butanoic acid, 3-oxo-, 1-methylethyl ester; Butanoicacid,3-oxo-,1-methylethylester; EINECS 208-798-4; Isopropyl 3-oxobutanoate; Isopropyl 3-Oxobutyrate; Isopropyl3-oxobutanoate; MFCD00043933; propan-2-yl 3-oxobutanoate;

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1.3 CAS No.: 542-08-5

1.4 CID: 68329

1.5 EINECS: 208-798-4

1.6 Molecular Formula: C7H12O3

1.7 Inchi: InChI=1S/C7H12O3/c1-5(2)10-7(9)4-6(3)8/h5H,4H2,1-3H3

1.8 InChkey: GVIIRWAJDFKJMJ-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)OC(=O)CC(=O)C

1.10 Isomers Smiles: CC(C)OC(=O)CC(=O)C

2. Properties

2.1 Appearance: Not Available

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: Colourless Liquid

2.4 pKa: 11.67±0.46(Predicted)

2.5 Water Solubility: Slightly miscible with water.

3. Use and Manufacturing

3.1 Description

Isopropyl acetoacetate, with the chemical formula C7H12O3, has the CAS number 542-08-5. It appears as a colorless liquid with a fruity odor. Its basic structure consists of an isopropyl group attached to an acetoacetate group. This compound is soluble in organic solvents such as ethanol and acetone, but sparingly soluble in water. Isopropyl acetoacetate is considered to be a relatively safe chemical with no known significant hazards or toxicity concerns. However, as with any chemical, it is important to handle it with care and follow proper safety precautions when working with it.

Applicable Fields

Pharmaceuticals: Isopropyl acetoacetate is commonly used as an intermediate in the synthesis of various pharmaceutical compounds. Its purpose in this field involves its ability to react with other chemicals to form complex organic molecules. The mechanism of action in pharmaceutical synthesis involves the formation of new chemical bonds and the modification of existing functional groups.

Flavors and Fragrances: This compound is also used in the production of flavors and fragrances. Its purpose in this field involves its ability to contribute to the desired aroma or taste profile of a product. The mechanism of action in flavors and fragrances involves the interaction of isopropyl acetoacetate with other aroma compounds or taste receptors.

Storage

Conditions: Store in a cool and dry place.

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3.2 Usage: Isopropyl acetoacetate (IPAA) is used as intermediate for chemical synthesis. Product Data Sheet

4. Safety and Handling

4.1 Safety: Hazard Codes: Xi
Risk Statements: 38
R38: Irritating to skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany of Isopropyl acetoacetate (CAS NO.542-08-5): 1

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4.2 Specification: Isopropyl acetoacetate (CAS NO.542-08-5), its Synonyms are Butanoic acid, 3-oxo-, 1-methylethyl ester ; 3-Oxo-butanoicaci1-methylethylester; Acetoaceticacid,isopropylester ; Acetoaceticacidisopropylester ; Isopropyl3-oxobutanoate . It is colourless liquid.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	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.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

542-08-5Total: 2 Synthesis Route

73200-00-7

73200-01-8

7737-62-4 6 Suppliers

542-08-5 80 Suppliers

141-97-9 355 Suppliers

73200-02-9

934-87-2 33 Suppliers

40053-29-0

67-63-0 129 Suppliers

108-21-4 161 Suppliers

542-08-5 80 Suppliers

8. Precursor and Product

precursor:

67-63-0

934-87-2

73200-00-7

73200-01-8

40053-29-0

product:

39562-25-9

14205-46-0

591-60-6

41096-59-7

245727-70-2

49748-30-3

64211-42-3

22136-61-4

66085-59-4

40596-69-8

9. Computed Properties

Molecular Weight：144.16838g/mol
Molecular Formula：C₇H₁₂O₃
Compound Is Canonicalized：True
Exact Mass：0.8
XLogP3-AA：144.078644241
Monoisotopic Mass：144.078644241
Complexity：138
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：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAACBSggAICCAAABAAIAICQCAAAAAAAAAAAAAEAAAAAABQIAAACAAAEIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: Isopropyl acetoacetate is used as an intermediate for the manufacturing of agrochemicals and pharmaceutical products such as isradipine.

Merck: 14,5206

BRN: 1757046

Chemical Properties: Colourless Liquid

Uses: Isopropyl acetoacetate (IPAA) is used as intermediate for chemical synthesis. Product Data Sheet

Application: Isopropyl acetoacetate can be used as a reactant to synthesize:
Isopropyl 2-acetyl-3-phenyl-2-propenoate via Knoevenagel reaction in the presence of Ti(O-i-Pr)4.
Substituted 1,4-dihydropyridines by reacting with cinnamaldehydes and primary amines.
5-Isopropoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione via Biginelli reaction with benzaldehyde and thiourea.

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Synthesis Reference(s): The Journal of Organic Chemistry, 26, p. 225, 1961 DOI: 10.1021/jo01060a055

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12. Related Questions

: How to Synthesize Isopropyl Acetoacetate Efficiently?Basic Information Isopropyl acetoacetate, also known as 3-butanone isopropyl acetoacetate or acetoacetic acid isopropyl ester, has the CAS number 542-08-5. Its molecular formula is C7H12O3 and molecul..

13. Realated Product Infomation