1522-46-9

Basic information

• Product Name: Ethyl 2-isopropylacetoacetate
• Synonyms: 2-Isopropylacetoacetic acid ethyl ester;Acetoacetic acid, 2-isopropyl-, ethyl ester;Ethyl 2-acetyl-3-methylbutanoate;ETHYL-ALPHA-ISOPROPYLACETOACETATE;ETHYL A-ISOPROPYLACETOACETATE;ETHYL-ISO-PROPYLACETOACETATE;ETHYL 2-ISO-PROPYLACETOACETATE;ethyl 2-acetyl-3-methylbutyrate
• CAS NO: 1522-46-9
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.22
• EINECS: 216-192-6
• Product Categories: C8 to C9;Carbonyl Compounds;Esters
• Mol File: 1522-46-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 82-85 °C12 mm Hg(lit.)
• Flash Point: 76 °C
• Appearance: Clear, colorless liquid.
• Density: 0.962 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.229mmHg at 25°C
• Refractive Index: n20/D 1.425
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate
• PKA: 12.28±0.46(Predicted)
• BRN: 636360
• CAS DataBase Reference: Ethyl 2-isopropylacetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-isopropylacetoacetate(1522-46-9)
• EPA Substance Registry System: Ethyl 2-isopropylacetoacetate(1522-46-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1522-46-9(Hazardous Substances Data)

Usage

Uses

Ethyl 2-Isopropylacetoacetate is a reactant in the preparation of nonracemic arylhydroxymethylpyrrolidinylmethylphenyl thiazoleacetamides and cyclopentathiazolecarboxamides as conformationally restricted β3-adrenoceptor agonists as a potential treatment for overactive bladder.

InChI:InChI=1/C9H16O3/c1-5-12-9(11)8(6(2)3)7(4)10/h6,8H,5H2,1-4H3/t8-/m1/s1

Upstream product

• 75-30-9 2-iodo-propane 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 108-20-3 di-isopropyl ether 
• 141-97-9 ethyl acetoacetate 
• 108-21-4 Isopropyl acetate 
• 67-63-0 isopropyl alcohol 
• 75-26-3 isopropyl bromide 
• 66279-50-3 ethylacetoacetate, K(+) salt 
• 64-17-5 ethanol 
• 67556-07-4 2-oxo-3-ethoxycarbonyl-3Z-pentene 
• 75-29-6 isopropyl chloride 

Downstream Products

• 19169-33-6 2-(4-Nitro-2-hydroxybenzolazo)-3-oxo-2-isopropylbuttersaeureaethylester 
• 42805-59-4 (Z)-3-Benzylamino-2-isopropyl-but-2-enoic acid ethyl ester 
• 29879-46-7 4-isopropyl-3-methyl-2H-isoxazol-5-one 
• 123-51-3 i-Amyl alcohol 
• 565-78-6 3,4-dimethyl-2-pentanone 
• 102440-15-3 5-isopropyl-6-methyl-pyridine-2,4-diol 
• 51756-10-6 Methyl 2-isopropyl-3-oxobutanoate 
• 1338062-50-2 3-isopropyl-3-(2,2-diphenylethenyl)tetrahydrofuran-2,4-dione 
• 1379596-65-2 4-{4-[2-amino-6-methyl-5-(1-methylethyl)pyrimidin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}benzene-1,2-diamine 
• 565-61-7 3-methyl-pentan-2-one 
• 108-10-1 4-methyl-2-pentanone 
• 516-06-3 D,L-valine 
• 7596-39-6 2-isopropylfumaric acid 
• 56116-35-9 2-ethyl-3-methylbutanol 

Relevant articles and documents

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MODULATOR OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR, PHARMACEUTICAL COMPOSITIONS, METHODS OF TREATMENT, AND PROCESS FOR MAKING THE MODULATOR

Compounds of Formula (I) pharmaceutically acceptable salts thereof, deuterated derivatives of any of the foregoing, and metabolites of any of the foregoing are disclosed. Pharmaceutical compositions comprising the same, methods of treating cystic fibrosis using the same, and methods for making the same are also disclosed. Also disclosed are solid state forms of Compound 1 and salts and solvates thereof.

Catalytic asymmetric synthesis of trisubstituted aziridines

A method is described which provides for the direct asymmetric catalytic synthesis of trisubstituted aziridines from imines and diazo compounds. While unactivated imines were not reactive to α-diazo carbonyl compounds in which the diazo carbon was disubstituted, N-Boc imines react with both α-diazo esters and α-diazo-N-acyloxazolidinones to give trisubstituted aziridines with excellent diastereo- and enantioselectivities.

Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives

Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the 1H NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4- diols and established that addition of hydrogen takes place selectively on the re-face of fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the 19F NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form.