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Isopropyl acetoacetate

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Isopropyl acetoacetate Basic information

Product Name:
Isopropyl acetoacetate
Synonyms:
  • 3-oxo-butanoicaci1-methylethylester
  • 3-Oxobutansαure-1-methylethylester
  • 3-Oxo-butyricacidisopropylester
  • Acetoaceticacid,isopropylester
  • acetoaceticacidisopropylester
  • Butanoicacid,3-oxo-,1-methylethylester
  • 3-oxobutanoic acid propan-2-yl ester
  • Isopropyl3-oxobutanoate
CAS:
542-08-5
MF:
C7H12O3
MW:
144.17
EINECS:
208-798-4
Product Categories:
  • Miscellaneous Reagents
  • C6 to C7
  • Carbonyl Compounds
  • Esters
  • bc0001
Mol File:
542-08-5.mol
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Isopropyl acetoacetate Chemical Properties

Melting point:
-27°C
Boiling point:
95 °C52 hPa(lit.)
Density 
0.989 g/mL at 20 °C(lit.)
refractive index 
n20/D 1.418
Flash point:
73°C
storage temp. 
Storage temp. 2-8°C
solubility 
Chloroform, Ethyl Acetate, Methanol, Toluene,
pka
11.67±0.46(Predicted)
form 
Colourless Liquid
color 
Colorless to Almost colorless
Water Solubility 
Slightly miscible with water.
Merck 
14,5206
BRN 
1757046
InChI
1S/C7H12O3/c1-5(2)10-7(9)4-6(3)8/h5H,4H2,1-3H3
InChIKey
GVIIRWAJDFKJMJ-UHFFFAOYSA-N
SMILES
CC(C)OC(=O)CC(C)=O
LogP
1.060 (est)
CAS DataBase Reference
542-08-5(CAS DataBase Reference)
EPA Substance Registry System
Butanoic acid, 3-oxo-, 1-methylethyl ester (542-08-5)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
38
Safety Statements 
26-36-24/25
WGK Germany 
1
TSCA 
TSCA listed
HS Code 
29183000
Storage Class
10 - Combustible liquids
Hazard Classifications
Skin Irrit. 2

MSDS

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Isopropyl acetoacetate Usage And Synthesis

Chemical Properties

Colourless Liquid

Uses

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

Uses

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

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 225, 1961 DOI: 10.1021/jo01060a055

Synthesis

In a 500 ml flask equipped with stirring, a thermometer and a reflux condenser tube, 150 g (2.5 mol) of isopropanol and 0.36 g of triethylamine were added, and 210 g (2.5 mol) of bis(vinylidene) ketone was added dropwise at room temperature, and the reaction temperature was controlled to be at 70 ?? during the reaction process, and at the end of the dropwise addition, the temperature was controlled to be at 70 ?? and kept warm for 6 hours to end the reaction. The crude ester was distilled under negative pressure to obtain the finished product isopropyl acetoacetate 343g, yield 95.2%, content 99.3%.

Isopropyl acetoacetate Preparation Products And Raw materials

Preparation Products

Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylatePROPETAMPHOSIsradipineIsopropyl 3-aminocrotonate

Isopropyl acetoacetateSupplier

Hubei Hongxin Ruiyu Fine Chemical Co., Ltd. Gold
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027-027-65526929 15102793023
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hbhxry@foxmail.com
BTC Pharmaceutical CO. Ltd Gold
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15716293042 18862996710
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15050603958@163.com
Hubei Wande Chemical Co., Ltd Gold
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027-027-59210159 15377098680
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Henan Dobe Chemical Co. , Ltd. Gold
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0370-6999054 17550096163
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3189729795@qq.com
J & K SCIENTIFIC LTD.
Tel
18210857532; 18210857532
Email
jkinfo@jkchemical.com
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