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Isopropyl acetoacetate
- Iupac Name：propan-2-yl 3-oxobutanoate
- CAS No.: 542-08-5
- Molecular Weight：144.16838
- Modify Date.: 2022-11-11 00:44
- Introduction:
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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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(EC#)
- 208-798-4
- 1.6 Molecular Formula
- C7H12O3 (isomer)
- 1.7 Inchi
- InChI=1S/C7H12O3/c1-5(2)10-7(9)4-6(3)8/h5H,4H2,1-3H3
- 1.8 InChIkey
- 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 Density
- 0.989
- 2.1 Melting point
- -27 oC
- 2.1 Boiling point
- 185.8 oC at 760 mmHg
- 2.1 Refractive index
- 1.413
- 2.1 Flash Point
- 68.9 oC
- 2.1 Precise Quality
- 144.07900
- 2.1 PSA
- 43.37000
- 2.1 logP
- 0.91710
- 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 Usage
- Isopropyl acetoacetate (IPAA) is used as intermediate for chemical synthesis. Product Data Sheet
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R38
- 4.1 Safety Statements
- 26-36
- 4.1 Hazard Declaration
- H315
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 WGK Germany
- 1
- 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
- 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.
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
7. Synthesis Route
542-08-5Total: 2 Synthesis Route
8. Other Information
- 8.0 Usage
- Isopropyl acetoacetate is used as an intermediate for the manufacturing of agrochemicals and pharmaceutical products such as isradipine.
- 8.1 Merck
- 14,5206
- 8.2 BRN
- 1757046
- 8.3 Chemical Properties
- Colourless Liquid
- 8.4 Uses
- Isopropyl acetoacetate (IPAA) is used as intermediate for chemical synthesis. Product Data Sheet
- 8.5 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.
- 8.6 Synthesis Reference(s)
- The Journal of Organic Chemistry, 26, p. 225, 1961 DOI: 10.1021/jo01060a055
9. Computational chemical data
- Molecular Weight: 144.16838g/mol
- Molecular Formula: C7H12O3
- Compound Is Canonicalized: True
- XLogP3-AA: 0.8
- Exact Mass: 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. Question & Answer
-
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..
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12. Realated Product Infomation
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